Benzoyl isothiocyanate → 2-[[(Benzoylamino)thioxomethyl)amino]-5-methylbenzamide

HRID 1091029Notes

Reaction equation

HRID 1091029 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:12]([N:20]=[C:21]=[S:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOCC>[C:12]([NH:20][C:21]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])=[S:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 103294362-Amino-5-methylbenzamide

Product 1

HCID 151355262-[[(Benzoylamino)thioxomethyl)amino]-5-methylbenzamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of 4.5 g of 2-amino-5-methylbenzamide and 200 ml of ether was added dropwise, a solution of 4.9 g of benzoyl isothiocyanate in 100 ml of ether over 20 minutes. After stirring overnight, the solid was collected, giving 8.7 g of 2-[[(benzoylamino)thioxomethyl]amino]-5-methylbenzamide.

Workup

  1. additionwas added dropwise
  2. customthe solid was collected

Sources & evidence

ORD record
ord-479bba923e5e43ffa1df1d47bdfec19e
Source dataset
uspto-grants-1992_01
Patent number
US05084457

Reaction notes

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