4-Methylbenzoyl isothiocyanate → N-Methyl-2-[[[(4-methylbenzoyl)amino]thioxomethyl]amino]benzamide

HRID 359530Notes

Reaction equation

HRID 359530 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[CH3:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([N:19]=[C:20]=[S:21])=[O:18])=[CH:15][CH:14]=1>CCOCC>[CH3:7][NH:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[NH:1][C:20]([NH:19][C:17](=[O:18])[C:16]1[CH:22]=[CH:23][C:13]([CH3:12])=[CH:14][CH:15]=1)=[S:21]

Participants

4

Reactant 2

HCID 1401394-Methylbenzoyl isothiocyanateHCID 3080722-Amino-N-methylbenzamide

Product 1

HCID 15135524N-Methyl-2-[[[(4-methylbenzoyl)amino]thioxomethyl]amino]benzamideYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of 8.0 g of 2-amino-N-methylbenzamide and 200 ml of ether was added dropwise, a solution of 10 g of 4-methylbenzoyl isothiocyanate in 100 ml of ether over 1 hour. After stirring several hours, the solid was collected, giving 17.1 g of the desired product as white crystals, mp 198°-200° C. (dec.).

Workup

  1. additionwas added dropwise
  2. customthe solid was collected

Sources & evidence

ORD record
ord-b448cc2c16c54ef08c36ca5decd5d6f1
Source dataset
uspto-grants-1991_03
Patent number
US05001157

Reaction notes

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