Ammonia → HCID 178425298, compound

HRID 1091027

Reaction equation

HRID 1091027 reaction equation
[NH2:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=S)[NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1)=[O:3].N>OO>[O:3]=[C:2]1[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:10][C:11]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)=[N:1]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 667545N-[(2-carbamoylphenyl)carbamothioyl]-3-methylbenzamide

Product 1

HCID 178425298HCID 178425298, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent2×

Procedure

To a stirred mixture of 9.3 g of the above benzamide and 200 ml of methanolic ammonia was added dropwise, 10 ml of 30% hydrogen peroxide over 3 minutes. An exotherm required cooling in an ice bath. A 15 ml portion of 30% hydrogen peroxide was added, the mixture was stirred 48 hours, the solid collected, and mixed with 100 ml of hot water. This solid was collected, mixed with 400 ml of hot acetonitrile and filtered. The filtrate was chilled, giving 2.3 g of the desired product as off-white crystals, mp 211°-213° C.

Workup

  1. additionwas added dropwise
  2. temperatureAn exotherm required cooling in an ice bath
  3. customthe solid collected
  4. additionmixed with 100 ml of hot water
  5. customThis solid was collected
  6. additionmixed with 400 ml of hot acetonitrile
  7. filtrationfiltered
  8. temperatureThe filtrate was chilled

Sources & evidence

ORD record
ord-8dc2e2cda81048fc8de8477320eae473
Source dataset
uspto-grants-1992_01
Patent number
US05084457

Linked notes

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