Benzoyl isothiocyanate → 2-[[(Benzylamino)thioxomethyl]amino]-N-phenylbenzamide

HRID 359539Notes

Reaction equation

HRID 359539 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[C:17]([N:25]=[C:26]=[S:27])(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[CH2:17]([NH:25][C:26]([NH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])=[S:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 781422-Amino-N-phenylbenzamide

Product 1

HCID 200651692-[[(Benzylamino)thioxomethyl]amino]-N-phenylbenzamideYield 1,015.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of 1.0 g of 2-amino-N-phenylbenzamide and 500 ml of ether was added dropwise, a solution of 7.7 g of benzoyl isothiocyanate in 100 ml of ether over 20 minutes. After standing several hours, the solid was collected, giving 17.3 g of the desired product as cream- colored crystals mp 197°-200° C. (dec.).

Workup

  1. additionwas added dropwise
  2. waitAfter standing several hours
  3. customthe solid was collected

Sources & evidence

ORD record
ord-8886c6374ee14ed0adc2d57d31ddb5d5
Source dataset
uspto-grants-1991_03
Patent number
US05001157

Reaction notes

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