Anthranilamide → 2-[(4-Chlorobenzoyl)carbamothioylamino]benzamide

HRID 1091024Notes

Reaction equation

HRID 1091024 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]=[C:9]=[S:10])=[O:7])=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17]>O1CCCC1>[NH2:18][C:16]([C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[NH:13][C:9](=[S:10])[NH:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:17]

Participants

4

Reactant 2

HCID 6942AnthranilamideHCID 2321624-Chlorobenzoyl isothiocyanate

Product 1

HCID 6676412-[(4-Chlorobenzoyl)carbamothioylamino]benzamideYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 10.5 g of 4-chlorobenzoyl isothiocyanate in 100 ml of tetrahydrofuran was added a mixture of 6.8 g of 2-aminobenzamide in 200 ml of tetrahydrofuran. After stirring for 3 hours the solid was collected, giving 14.3 g of N-[[[2-(aminocarbonyl)phenyl]amino]thioxomethyl]-4-chlorobenzamide.

Workup

  1. additionwas added
  2. customwas collected

Sources & evidence

ORD record
ord-13eafc519e2141b2bada6c0220b1e8d7
Source dataset
uspto-grants-1992_01
Patent number
US05084457

Reaction notes

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