Ammonia → 1-(Trimethylsilyl)-3-[(trimethylsilyl)sulfanyl]-1H-1,2,4-triazole

HRID 2413337Notes

Reaction equation

HRID 2413337 reaction equation
C[Si](C)(C)[NH:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[SH:10][C:11]1[N:15]=[CH:14]N[N:12]=1.N>ClCCl>[CH3:7][Si:4]([CH3:5])([CH3:6])[N:3]1[CH:14]=[N:15][C:11]([S:10][Si:4]([CH3:7])([CH3:6])[CH3:5])=[N:12]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13838HexamethyldisilazaneHCID 178527894HCID 178527894, compound

Product 1

HCID 204308151-(Trimethylsilyl)-3-[(trimethylsilyl)sulfanyl]-1H-1,2,4-triazoleYield 134.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-trimethylsilyl-3-trimethylsilylthio-1H-1,2,4-triazole was prepared by adding 29.2 ml (140 mmoles) of hexamethyldisilazane to a refluxing suspension of 9.70 g (96 mmoles) of 3-mercapto-1H-1,2,4-triazole and 100 mg (0.25 mmole) of di-4-nitrophenyl-N-(4-toluenesulfonyl)-phosphoramidate in 200 ml of dichloromethane and the calculated amount of ammonia was evolved after refluxing for 75 minutes. Refluxing was continued for 30 minutes and then the clear solution obtained was evaporated to dryness to obtain 23.1 g (98% yield) of 1-trimethylsilyl-3-trimethylsilylthio-1H-1,2,4-triazole melting at 90°-94° C.

Workup

  1. custom1-trimethylsilyl-3-trimethylsilylthio-1H-1,2,4-triazole was prepared
  2. temperatureafter refluxing for 75 minutes
  3. temperatureRefluxing
  4. customthe clear solution obtained
  5. customwas evaporated to dryness

Sources & evidence

ORD record
ord-e5f861150762424c8c7b6b8930f1091b
Source dataset
uspto-grants-1985_01
Patent number
US04496720

Reaction notes

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