2-(phenylsulfanyl)acetaldehyde -Drug Synthesis Database

【结构式】

【分子编号】19434

【品名】2-(phenylsulfanyl)acetaldehyde

【CA登记号】

【分子式】C₈H₈OS

【分子量】152.21692

【元素组成】C 63.13% H 5.3% O 10.51% S 21.07%

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：(III)

1) The diazotation of 4-amino-N-methylbenzenemethanesulfonamide (I) with NaNO2-HCl followed by reduction with SnCl2 gives the 4-hydrazino compound (II), which is condensed with (phenylthio)acetaldehyde (III) in ethanol yielding the ethylideneamino compound (IV). The cyclization of (IV) with HCl in ethanol affords N-methyl-3-(phenylthio)-1H-indole-5-methansulfonamide (V), which is desulfurized with RaNi in refluxing ethanol-water to give N-methyl-1H-indole-5-methanesulfonamide (VI). The reaction of (VI) with oxalyl chloride and dimethylamine yields the oxalyl derivative (VII), which is finally reduced with LiAlH4 in refluxing THF.

参考文献中间体

合成目标

【1】 Oxford, A.W. (Glaxo Group Ltd.); An indole derivative.. GB 2162522 .
【2】 Coates, I.H.; Dowle, M.D. (Glaxo Group Ltd.); Heterocyclic compounds.. FR 2530625; GB 2124210; US 4816470 .
【3】 Humphrey, P.P.A.; Feniuk, W.; Perren, M.J.; Oxford, A.W.; Brittain, R.T.; Prous, J.; Castaner, J.; SUMATRIPTAN SUCCINATE < Prop INNM; BAN >. Drugs Fut 1989, 14, 1, 35.

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)	19432	(4-aminophenyl)-N-methylmethanesulfonamide; 4-amino-N-ethylbenzylmethanesulfamide	109903-35-7	C₈H₁₂N₂O₂S	详情	详情
(II)	19433	(4-hydrazinophenyl)-N-methylmethanesulfonamide	88933-16-8	C₈H₁₃N₃O₂S	详情	详情
(III)	19434	2-(phenylsulfanyl)acetaldehyde		C₈H₈OS	详情	详情
(IV)	19435	N-methyl(4-[2-[(E)-2-(phenylsulfanyl)ethylidene]hydrazino]phenyl)methanesulfonamide		C₁₆H₁₉N₃O₂S₂	详情	详情
(V)	19436	N-methyl[3-(phenylsulfanyl)-1H-indol-5-yl]methanesulfonamide		C₁₆H₁₆N₂O₂S₂	详情	详情
(VI)	19437	1H-indol-5-yl-N-methylmethanesulfonamide		C₁₀H₁₂N₂O₂S	详情	详情
(VII)	19438	N,N-dimethyl-2-(5-[[(methylamino)sulfonyl]methyl]-1H-indol-3-yl)-2-oxoacetamide		C₁₄H₁₇N₃O₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

3) The condensation of indole (VI) with N,N-diethylchloroacetamide (X) by means of POCl3 gives 3-chloroacetyl-N-methyl-1H-indole-5-methanesulfonamide (XI), which is treated with dimethylamine (XII) in refluxing ethanol to afford the dimethylaminoacetyl derivative (XIII), which is finally reduced with NaBH4 in refluxing propanol.

参考文献中间体

合成目标

【1】 Oxford, A.W. (Glaxo Group Ltd.); An indole derivative.. GB 2162522 .
【2】 Coates, I.H.; Dowle, M.D. (Glaxo Group Ltd.); Heterocyclic compounds.. FR 2530625; GB 2124210; US 4816470 .
【3】 Humphrey, P.P.A.; Feniuk, W.; Perren, M.J.; Oxford, A.W.; Brittain, R.T.; Prous, J.; Castaner, J.; SUMATRIPTAN SUCCINATE < Prop INNM; BAN >. Drugs Fut 1989, 14, 1, 35.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	19441	2-chloro-N,N-diethylacetamide	2315-36-8	C₆H₁₂ClNO	详情	详情
(I)	19432	(4-aminophenyl)-N-methylmethanesulfonamide; 4-amino-N-ethylbenzylmethanesulfamide	109903-35-7	C₈H₁₂N₂O₂S	详情	详情
(II)	19433	(4-hydrazinophenyl)-N-methylmethanesulfonamide	88933-16-8	C₈H₁₃N₃O₂S	详情	详情
(III)	19434	2-(phenylsulfanyl)acetaldehyde		C₈H₈OS	详情	详情
(IV)	19435	N-methyl(4-[2-[(E)-2-(phenylsulfanyl)ethylidene]hydrazino]phenyl)methanesulfonamide		C₁₆H₁₉N₃O₂S₂	详情	详情
(V)	19436	N-methyl[3-(phenylsulfanyl)-1H-indol-5-yl]methanesulfonamide		C₁₆H₁₆N₂O₂S₂	详情	详情
(VI)	19437	1H-indol-5-yl-N-methylmethanesulfonamide		C₁₀H₁₂N₂O₂S	详情	详情
(XI)	19442	[3-(2-chloroacetyl)-1H-indol-5-yl]-N-methylmethanesulfonamide		C₁₃H₁₅ClN₂O	详情	详情
(XII)	19443	N-methylmethanamine; N,N-dimethylamine	124-40-3	C₂H₇N	详情	详情
(XIII)	19444	[3-[2-(dimethylamino)acetyl]-1H-indol-5-yl]-N-methylmethanesulfonamide		C₁₄H₁₉N₃O₃S	详情	详情

Extended Information