- Synthesis and Crystal Structures of Diaryl Thioethers and Aryl Benzyl Thioethers Derived from Thiosalicylic Acid
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Abstract: Reaction of thiosalicylic acid and iodobenzene or 1-fluoro-2-nitrobenzene in the presence of two equiv. of K2CO3 in acetone–water afforded the according diaryl thioethers 1 and 2 bearing carboxyl groups. Treatment of thiosalicylic acid with benzyl bromide-type compounds under similar reaction conditions gave aryl benzyl thioethers 3–8 in excellent yields. Moreover, reactions of thiosalicylic acid and benzyl bromide in the presence of excess K2CO3 led to isolation of compound 9 (Leka et al. in Acta Cryst E69:o285–0286, 2013) through further esterification of the carboxyl group. Crystal structures of 2, 5–7 and 9 (Leka et al. in Acta Cryst E69:o285–0286, 2013), along with their spectroscopic properties are reported. Weak hydrogen-bonding interactions exist in compound 2 and isomers 5–7. Compounds 2 and 7 crystallize in the monoclinic space group P21/n and C2/c, respectively, with a = 12.04(3), b = 7.311(19), C=14.22(4) ?, β = 93.94(3)°, and Z = 4 for 2, and a = 14.934(13), b = 5.116(5), C=33.76(3) ?, β = 91.523(12)°, and Z = 8 for 7. The unit cell of 5 has triclinic P-1 symmetry with the cell parameters a = 5.4334(14), b = 7.7787(19), C=16.488(4) ?, α = 76.601(3)°, β = 86.078(3)°, γ = 70.772(3)°, and Z = 2 for 5. Compound 6 crystallizes in the orthorhombic space group Pbca with a = 15.1881(12), b = 7.3288(6), C=23.7366(19) ?, and Z = 8. Graphical Abstract: Reactions of thiosalicylic acid and a series of aryl- or benzyl halides in the presence of K2CO3 in acetone–water resulted in the formation of according diaryl thioethers and aryl benzyl thioethers in excellent yields.
- Liu, Dan,Chen, Min,Fang, Duowen,Jia, Ai-Quan,Zhang, Qian-Feng
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- Antibodies to quetiapine haptens and use thereof
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Disclosed is an antibody which binds to quetiapine, which can be used to detect quetiapine in a sample such as in a competitive immunoassay method. The antibody can be used in a lateral flow assay device for point-of-care detection of quetiapine, including multiplex detection of aripiprazole, olanzapine, quetiapine, and risperidone in a single lateral flow assay device.
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Page/Page column 41
(2018/01/20)
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- A process for the preparation of intermediates quetiapine (by machine translation)
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The invention discloses a preparation method for a quetiapine intermediate. The preparation method comprises: taking thiosalicylic acid as an initial raw material to prepare 2-nitro-2'-carboxyldiphenyl sulfide, esterifying and reducing, and then performing intramolecular amino-ester exchange reaction for cyclization, so as to obtain the quetiapine intermediate 10,11-dihydro-11-oxodibenzo[b,f][1,4]thiazepine. The preparation method is simple, the target product is high in purity, the reaction yield is relatively high, the production cost is effectively reduced, and industrialized production of the high-purity quetiapine intermediate is facilitated to be realized.
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Paragraph 0018-0019
(2017/02/24)
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- A [...] synthesis process (by machine translation)
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The present invention discloses a process for synthesizing [...], comprises the following steps: compound of formula (II), C1 - C4 acid mixed, and heated to 80 - 100 °C, adding zinc powder or iron powder, thermal insulation reaction 4 - 6h, shall quetiapine; with the resulting quetiapine fumaric acid salifying, [...], wherein quetiapine with fumaric acid feeding molar ratio of 1: 0.5. The process of the invention has simple operation, high yield, the resulting high purity of the product advantages, and is easy to realize industrial. (by machine translation)
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Paragraph 0021; 0033; 0055
(2017/02/17)
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- Antibodies to Quetiapine Haptens and Use Thereof
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Disclosed is an antibody which binds to quetiapine, which can be used to detect quetiapine in a sample such as in a competitive immunoassay method. The antibody can be used in a lateral flow assay device for point-of-care detection of quetiapine, including multiplex detection of aripiprazole, olanzapine, quetiapine, and risperidone in a single lateral flow assay device.
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Page/Page column
(2014/03/24)
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- HAPTENS OF QUETIAPINE FOR USE IN IMMUNOASSAYS
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The invention relates to compounds of Formula I, wherein R1, R2, and R3 are defined in the specification, useful for the synthesis of novel conjugates and immunogens derived from quetiapine. The invention also relates to conjugates of a quetiapine hapten and a protein.
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Page/Page column 55
(2014/03/25)
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- IRON CATALYZED CROSS-COUPLING REACTIONS OF IMIDOYL DERIVATIVES
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Disclosed is a process for preparing a compound of formula A - N=C(D)(B), from a compound of formula A-N=C(E)(B) and a compound of formula D-M using an iron catalyst, where the process has is represented by Equation (I).
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Page/Page column 19; 52
(2010/11/27)
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- Process for preparing dibenzothiazepine compounds
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A dibenzothiazepine compound is suitably prepared by subjecting a 2-amino-2′-carboxy-diphenylsulfide compound to dehydration-condensation reaction in the presence of an acidic catalyst; the 2-amino-2′-carboxy-diphenylsulfide compound is suitably prepared by reducing a 2-nitro-2′-carboxy-diphenylsulfide compound in a lower aliphatic ester solvent; and the 2-nitro-2′-carboxy-diphenylsulfide compound is suitably prepared by reacting a nitrobenzene compound with a thiosalicylic acid compound in a mixture of a lower aliphatic alcohol and water.
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Page/Page column 7
(2008/06/13)
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- PROCESS FOR THE PREPARATION OF 11-(4-[2-(2-HYDROXYETHOXY)ETHYL]-I-PIPERAZINYL)DIB ENZO[b,f][l,4]THIAZEPINE
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Disclosed is a process for the preparation of l l-(4-[2-(2-hydroxyethoxy)ethyl]-l- piperazinyl)-dibenzo[b,f][l,4]thiazepine. In the process, low-priced 2,2'-dithiosalicylic acid as starting material is subjected to bond formation reaction with l-chloro-2-
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Page/Page column 13
(2010/02/15)
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- PROCESS FOR PRODUCING 11-[4-[2-(2-HYDROXYETHOXY)ETHYL]-1-PIPERAZINYL]DIBENZO[b,f][1,4]THIAZEPINE AND A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
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A process for producing 11-[4-[2-(2-hydroxyethoxy)ethyl]-l-piperazinyl]dibenzo [b,f][1,4]thiazepine [I] and a pharmaceutically suitable acid addition salt is disclosed. Accordingly, thiosalicylic acid [XVI] is reacted with o-halonitrobenzene [XVII] using a phase transfer catalyst to obtain 2-nitro-2'-carboxydiphenylsulphide [XI]. It is hydrogenated in the presence of a noble metal catalyst to obtain 2-amino-2' carboxydiphenyl sulphide [X]. The 2-amino-2'-carboxydiphenylsulphide [X] is reacted with halide or oxyhalide of the phosphorous to obtain in situ iminohalide [VI], which further reacts as such with 1-hydroxyethoxyethylpiperazine or condenses with piperazine to obtain 11-piperazinyldi.benzo[b,f][1,4]thiazepine [XIX] which further reacts with 2- chloroethoxyethanol or reacts with 1-(2-hydroxyethyl)piperazine to give 11-[4-(2-hydroxyethyl)piperazine-1-yl]dibenzo[b,f][ 1,4]thiazepine [XXXI] which further converts to an intermediate 11-[4-(2-substitutedethyl)piperazin-1- yl)dibenzo[b,f][1,4]thiazepine wherein the substituent at the 2-position is selected from mesyloxy or tosyloxy or halo group [XXXII] followed by reaction with ethylene glycol to give quetiapine [1].
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Page/Page column 9; 14
(2008/06/13)
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- Process for the preparation of a thiazepine derivative
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The present invention relates to a process for the preparation of biologically active thiazepine derivative. The present invention more particularly, relates to an improved process for the preparation of dibenzo[b,f][1,4]thiazepine derivative of formula (I).
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Page/Page column 5
(2010/02/11)
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- Synthesis, in vitro characterization, and radiolabeling of N,N-dimethyl-2-(2′-amino-4′-substituted-phenylthio)benzylamines: Potential candidates as selective serotonin transporter radioligands
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A series of N,N-dimethylated and N-monomethylated analogues of N,N-dimethyl-2-(2′-amino-4′-iodophenylthio)benzylamine substituted at the 4′-phenyl position have been prepared and evaluated in vitro for serotonin transporter (SERT) selectivity. Several der
- Jarkas, Nachwa,McConathy, Jonathan,Voll, Ronald J.,Goodman, Mark M.
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p. 4254 - 4265
(2007/10/03)
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- PROCESS FOR PRODUCING DIBENZOTHIAZEPINE DERIVATIVES
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A process for preparing a dibenzothiazepine derivative such as dibenzo[b,f] [1,4]thiazepin-11-one employable as a starting material for the preparation of 11-[4-(2-(2-hydroxyethoxy)ethyl)]-1-piperadinyldiberizothiazepine derivative which is known to be effective as an antipsychotic pharmaceutical, has the steps of reacting a nitrobenzene derivative with a thiosalicylic acid derivative, reducing the obtained 2-nitro-2'-carboxy-diphenylsulfide derivative, and subjecting the obtained 2-amino-2'-carboxy-diphenylsulfide derivative to dehydration-condensation reaction.
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- NOVEL REACTIONS OF SPIROSULFURANE PRECURSOR SULFIDES AND SULFOXIDES
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The SIV spirosulfurane 19 and the lactam-sulfoxides 21, 22 and 23 with seven-, eight- and nine-membered rings have been prepared by oxidation and dehydration of trifluoroacetylaminoarylcarboxyphenyl sulfides and sulfoxides, respectively.A mechanism is proposed for the formations of lactam-sulfoxides.The preparation of the starting sulfides and sulfoxides is also described. Key words: Diaryl sulfides; diaryl sulfoxides; spirosulfurane; lactams; carboxyl activation; lactam-sulfoxide formation.
- Kuti, M.,Rabai, J.,Kapovits, I.
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p. 119 - 128
(2007/10/02)
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