Ammonia → N-trimethylsilylurethane

HRID 435191Notes

Reaction equation

HRID 435191 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si](C)(C)C.N[C:11]([O:13][CH2:14][CH3:15])=[O:12].N>S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O.C1(C)C=CC=CC=1>[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5641Carbamic acid, ethyl esterHCID 13838Hexamethyldisilazane

Product 1

HCID 11355656N-trimethylsilylurethaneYield 129%

Reagents, catalysts & solvents 2

HCID 5143SaccharinCatalystHCID 1140TolueneSolvent

Procedure

15.6 ml of hexamethyldisilazane (0.075 mole) were added over 2 minutes to a refluxing mixture of 8.9 g (0.1 mole) of urethane, 183 mg (1 mmole) of saccharin and 10 ml of toluene and the theoretical amount of ammonia was evolved in 30 minutes. Refluxing was continued for 15 minutes and the solvent and excess hexamethyldisilazane were removed under reduced pressure. The residue was vacuum distilled to obtain 15.6 g (96.9%) of N-trimethylsilylurethane boiling at 73° C. at 12 mm Hg and nD 25=1.4268.

Workup

  1. temperatureRefluxing
  2. customthe solvent and excess hexamethyldisilazane were removed under reduced pressure
  3. distillationdistilled

Sources & evidence

ORD record
ord-dcdf5a86e6d246da8c89c3c05a6d955b
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Reaction notes

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