Ammonia → 1-Trimethylsilyl-5-trimethylsilylthio-1,2,3-triazole

HRID 435186Notes

Reaction equation

HRID 435186 reaction equation
C[Si](C)(C)[NH:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[SH:10][C:11]1N[N:14]=[N:13][CH:12]=1.S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O.N.OS(O)(=O)=O>ClCCl.C(OCC)(=O)C>[CH3:7][Si:4]([CH3:5])([CH3:6])[N:3]1[C:11]([S:10][Si:4]([CH3:7])([CH3:6])[CH3:5])=[CH:12][N:13]=[N:14]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 5143SaccharinHCID 13838HexamethyldisilazaneHCID 178527741HCID 178527741, compound

Product 1

HCID 204910741-Trimethylsilyl-5-trimethylsilylthio-1,2,3-triazoleYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.52 ml of hexamethyldisilazane (7.3 mmoles) were added to a refluxing mixture of 0.49 (4.86 mmoles) of 5-mercapto-1,2,3-(1H)-triazole, 5 mg (0.207 mmole) of saccharin, 10 ml of ethyl acetate and 15 ml of dichloromethane and the ammonia evolved was titrated with 1 N H2SO4 by the method described in Example 1A. It was found that 2 equivalents (4.9 mmoles) were evolved after refluxing for 30 minutes. Volatile materials were evaporated in vacuo to obtain 1.19 g (96%) of 1-trimethylsilyl-5-trimethylsilylthio-1,2,3-triazole NMR Spectrum was taken in carbon tetrachloride solution: Δ0.31 (9H); 0.48 (9H); 7.46 (1H).

Workup

  1. temperatureafter refluxing for 30 minutes
  2. customVolatile materials were evaporated in vacuo

Sources & evidence

ORD record
ord-21c661c5a5a14e94a8fd2c81eb121e57
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Reaction notes

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