Ammonia → Silanamine, 1,1,1-trimethyl-N-(4-methylphenyl)-

HRID 435185Notes

Reaction equation

HRID 435185 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si](C)(C)C.N[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.N>S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O>[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 7813p-ToluidineHCID 13838Hexamethyldisilazane

Product 1

HCID 11008511Silanamine, 1,1,1-trimethyl-N-(4-methylphenyl)-Yield 111.5%

Reagents, catalysts & solvents 1

HCID 5143SaccharinCatalyst

Conditions

Temperature
130 °C

Procedure

25 ml of hexamethyldisilazane (0.12 mole) were added in 5 minutes to a mixture of 17.25 g (0.16 mole) of p-toluidine and 0.15 g (0.8 mmole) of saccharin which was heated to 130° C. in an oil bath. By titrating the ammonia evolved during the reaction, it was found that the calculated amount was evolved after refluxing for 2 hours and refluxing was continued for half an hour. The reaction mixture was vacuum distilled to yield 24.0 g (83%) of N-trimethylsilyl-p-toluidine with a boiling point of 98°-102° C. at 12-13 mm Hg.

Workup

  1. customevolved during the reaction, it
  2. temperatureafter refluxing for 2 hours
  3. temperaturerefluxing
  4. waitwas continued for half an hour
  5. distillationdistilled

Sources & evidence

ORD record
ord-4e62538f0eb749598390fc439ce79518
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Reaction notes

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