4-(Methylamino)benzonitrile → 2-[N-(4-cyanophenyl)-N-me-thylaminomethyl]benzothiazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

HRID 2288346Notes

Reaction equation

HRID 2288346 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([NH:7][CH3:8])=[CH:5][CH:4]=1)#[N:2].[C:11]1([N:17]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:18]([C:20]2[CH:21]=[CH:22][C:23]3[S:27][C:26]([CH2:28]OC)=[N:25][C:24]=3[CH:31]=2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl.C(O)C>[C:11]1([N:17]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:18]([C:20]2[CH:21]=[CH:22][C:23]3[S:27][C:26]([CH2:28][N:7]([C:6]4[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)[CH3:8])=[N:25][C:24]=3[CH:31]=2)=[O:19])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 109645514-(Methylamino)benzonitrileHCID 184125442-methoxymethylbenzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

Product 1

HCID 544508072-[N-(4-cyanophenyl)-N-me-thylaminomethyl]benzothiazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amideYield 57%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 9e from 4-cyano-N-methyl-aniline and 2-methoxymethyl-benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide. Yield: 57% of theory, Rf value: 0.46 (silica gel; dichloromethane/ethanol=19:1).

Sources & evidence

ORD record
ord-e3897cec270e4ebfb082c441f7709bb8
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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