1,2-dichloro-4-isocyanatobenzene; 3,4-dichlorophenyl isocyanate -Drug Synthesis Database

【结构式】

【分子编号】34282

【品名】1,2-dichloro-4-isocyanatobenzene; 3,4-dichlorophenyl isocyanate

【CA登记号】102-36-3

【分子式】C₇H₃Cl₂NO

【分子量】188.01236

【元素组成】C 44.72% H 1.61% Cl 37.71% N 7.45% O 8.51%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The oxidation of 7-chloro-5-hydroxy-2,3-dihydro-1-benzothiepin (I) with H2O2 in acetic acid - water gives 7-chloro-5-hydroxy-2,3-dihydro-1-benzothiepin-1,1-dioxide (II), which by reaction with pyrrolidine (III) and p-toluenesulfonic acid in refluxing benzene is converted into 7-chloro-5-pyrrolidino-2,3-dihydro-1-benzothiepin-1,1-dioxide (IV). The condensation of (IV) with 3,4-dichlorophenyl isocyanate (V) in hot THF yields N-(3,4-dichlorophenyl)-7-chloro-5-pyrrolidino-2,3-dihydro-1-benzothiepin-4-carboxamide-1,1-dioxide (VI), which is finally hydrolyzed with HCl in refluxing ethanol - water.

参考文献中间体

合成目标

【1】 Rosen, M.H.; 1-Benzothiepin-4-carboxamides. BE 0833787; CA 1066279; CH 617433; DE 2542329; FR 2285872; US 4185109 .
【2】 Serradell, M.N.; Castaner, J.; Enolicam sodium. Drugs Fut 1984, 9, 7, 508.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	34279	7-chloro-2,3-dihydro-1-benzothiepin-5-ol		C₁₀H₉ClOS	详情	详情
(II)	34280	7-chloro-5-hydroxy-2,3-dihydro-1H-2H-benzothiepine-1,1-dione		C₁₀H₉ClO₃S	详情	详情
(III)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(IV)	34281	7-chloro-5-(1-pyrrolidinyl)-2,3-dihydro-1H-2H-benzothiepine-1,1-dione		C₁₄H₁₆ClNO₂S	详情	详情
(V)	34282	1,2-dichloro-4-isocyanatobenzene; 3,4-dichlorophenyl isocyanate	102-36-3	C₇H₃Cl₂NO	详情	详情
(VI)	34283	7-chloro-N-(3,4-dichlorophenyl)-1,1-dioxo-5-(1-pyrrolidinyl)-2,3-dihydro-1H-2H-benzothiepine-4-carboxamide		C₂₁H₁₉Cl₃N₂O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Electrophilic sulfonation of 2,3-dihydrobenzofuran (I) using sulfur trioxide-dimethylformamide complex produced sulfonic acid (II), which was subsequently converted into the sulfonyl chloride (III) by chlorination with SOCl2. Reaction of sulfonyl chloride (III) with a solution of ammonia in cold dichloroethane gave rise to the sulfonamide (IV). This was subsequently condensed with 3,4-dichlophenyl isocyanate (V) to furnish the target sulfonyl urea

参考文献中间体

合成目标

【1】 Tao, E.V.-P.; Miller, W.D. (Eli Lilly and Company); Synthesis of bicyclic aromatic sulfonic acids, sulfonyl chlorides and sulfonamides. EP 0583960 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	14499	2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran	496-16-2	C₈H₈O	详情	详情
(II)	59847	2,3-dihydro-1-benzofuran-5-sulfonic acid		C₈H₈O₄S	详情	详情
(III)	59848	2,3-dihydro-1-benzofuran-5-sulfonyl chloride		C₈H₇ClO₃S	详情	详情
(IV)	59849	2,3-dihydro-1-benzofuran-5-sulfonamide		C₈H₉NO₃S	详情	详情
(V)	34282	1,2-dichloro-4-isocyanatobenzene; 3,4-dichlorophenyl isocyanate	102-36-3	C₇H₃Cl₂NO	详情	详情

Extended Information