[5-chloro-2-(methylamino)phenyl](phenyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】33972

【品名】[5-chloro-2-(methylamino)phenyl](phenyl)methanone

【CA登记号】1022-13-5

【分子式】C₁₄H₁₂ClNO

【分子量】245.70812

【元素组成】C 68.44% H 4.92% Cl 14.43% N 5.7% O 6.51%

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：(II)

The methylation of 2-amino-5-chlorobenzophenone (I) with dimethyl-sulfate affords the 5-chloro-2-methylaminobenzophenone (II), which is conden-sed with bromoacetyl bromide (A) to yieId 2-(2-bromo-N-methylacetamido)-5-chlorobenzophenone (III). The amonolysis of (III) with ammonia in methanol gives 2-(2-amino-N-methylacetamido)-5-chlorobenzophenone (IV), which is finally condensed with diketene (B) in refluxing acetone. This product can also be obtained by condensation of 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (V) with acetyl chloride (C) and triethylamine in ether or with diketene (B) in acetone.

参考文献中间体

合成目标

【1】 Szmuszkovicz, J.; et al.; Tetrahedron Lett 1971, 39, 39, 3665.
【2】 Szmuszkovicz, J.; Oxazinobenzodiazepine derivatives. DE 1947226; ES 371392; FR 2018432; GB 1222294 .
【3】 Szmuszkovicz, J.; Process for the preparation of 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-[1,3]oxazino[3,2-d]benzodiazepine-4,7-6H-dione. CH 530414; JP 49025953B; NL 7014824; US 3575965 .
【4】 Castaner, J.; Chatterjee, S.S.; Ketazolam. Drugs Fut 1976, 1, 6, 293.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	11367	4-Methylene-2-oxetanone; Acetyl ketene	674-82-8	C₄H₄O₂	详情	详情
(A)	14005	2-Bromoacetyl bromide; Bromoacetyl bromide	598-21-0	C₂H₂Br₂O	详情	详情
(I)	10279	(2-Amino-5-chlorophenyl)(phenyl)methanone; 2-Amino-5-chlorobenzophenone	719-59-5	C₁₃H₁₀ClNO	详情	详情
(II)	33972	[5-chloro-2-(methylamino)phenyl](phenyl)methanone	1022-13-5	C₁₄H₁₂ClNO	详情	详情
(III)	33973	N-(2-benzoyl-4-chlorophenyl)-2-bromo-N-methylacetamide		C₁₆H₁₃BrClNO₂	详情	详情
(IV)	33974	2-amino-N-(2-benzoyl-4-chlorophenyl)-N-methylacetamide		C₁₆H₁₅ClN₂O₂	详情	详情
(V)	33975	7-chloro-1-methyl-5-phenyl-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one		C₁₆H₁₅ClN₂O	详情	详情
(C)	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The tosylation of 2-amino-5-chlorobenzophenone (I) with tosyl chloride (II) in pyridine gives 2-tosylamido-5-chlorobenzophenone (III), which is methylated with dimethyl sulfate and sodium methoxide in toluene yielding N-methyl-2-tosylamido-5-chlorobenzophenone (IV). Hydrolysis of (IV) with aqueous sulfuric acid affords 2-methylamino-5-chlorobenzophenone (V), which is acylated with bromoacetyl chloride (VI) in benzene to give N-methyl-2-(bromoacetylamido)-5-chlorobenzophenone (VII). Finally this compound is condensed with 2-methylallylamine (VIII) in acetone

参考文献中间体

合成目标

【1】 Mouzin, G.; Cousse, H.; Stenger, A.; Casadio, S. (Pierre Fabre S.A.); US 4372975 .
【2】 Serradell, M.N.; Castaner, J.; Souto, M.; Dinazafone. Drugs Fut 1984, 9, 7, 501.

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)	10279	(2-Amino-5-chlorophenyl)(phenyl)methanone; 2-Amino-5-chlorobenzophenone	719-59-5	C₁₃H₁₀ClNO	详情	详情
(II)	25151	phenylmethanesulfonyl chloride	1939-99-7	C₇H₇ClO₂S	详情	详情
(III)	61085	N-(2-benzoyl-4-chlorophenyl)(phenyl)methanesulfonamide		C₂₀H₁₆ClNO₃S	详情	详情
(IV)	61086	N-(2-benzoyl-4-chlorophenyl)-N-methylphenylmethanesulfonamide		C₂₁H₁₈ClNO₃S	详情	详情
(V)	33972	[5-chloro-2-(methylamino)phenyl](phenyl)methanone	1022-13-5	C₁₄H₁₂ClNO	详情	详情
(VI)	27903	2-Bromoacetyl chloride	22118-09-8	C₂H₂BrClO	详情	详情
(VII)	33973	N-(2-benzoyl-4-chlorophenyl)-2-bromo-N-methylacetamide		C₁₆H₁₃BrClNO₂	详情	详情
(VIII)	61087	2-methyl-2-propen-1-amine; 2-methyl-2-propenylamine		C₄H₉N	详情	详情

Extended Information