Ammonia → N-trimethylsilyl-4-nitrobenzamide

HRID 435189

Reaction equation

HRID 435189 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si](C)(C)C.[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](N)=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11].C1C=C2C3=C(C(NC(=O)C3=CC=C2)=O)C=1.N>C(OCCCC)(=O)C>[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][C:17](=[O:18])[C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 120914-NitrobenzamideHCID 13838HexamethyldisilazaneHCID 66491Naphthalimide

Product 1

HCID 12726300N-trimethylsilyl-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Procedure

4.5 ml of hexamethyldisilazane (22 mmoles) were added to a refluxing mixture of 5.0 g (30.1 mmoles) of 4-nitrobenzamide, 100 mg (0.5 mmole) of 1.8-naphthalimide and 20 ml of butyl acetate and the calculated amount of ammonia was evolved after refluxing for 35 minutes. The same experiment without catalyst was carried out and only 16% of the theoretical amount of ammonia was evolved after refluxing for 15 minutes. After refluxing for 1 hour, 83% of that amount of evolved.

Workup

  1. temperatureafter refluxing for 35 minutes
  2. temperatureafter refluxing for 15 minutes
  3. temperatureAfter refluxing for 1 hour

Sources & evidence

ORD record
ord-f9c9ab949fa740f8b6236a8a66d7f676
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Linked notes

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