Bromochloromethane → 5-Chloromethylthio-1-methyltetrazole

HRID 1196869Notes

Reaction equation

HRID 1196869 reaction equation
O.[SH:2][C:3]1[N:7]([CH3:8])[N:6]=[N:5][N:4]=1.[Na].Br[CH2:11][Cl:12]>CC#N>[Cl:12][CH2:11][S:2][C:3]1[N:7]([CH3:8])[N:6]=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 6333BromochloromethaneHCID 178482031HCID 178482031, compound

Product 1

HCID 103520355-Chloromethylthio-1-methyltetrazoleYield 77.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of sodium 5-mercapto-1-methyltetrazole hydrate (1.38 g, 10.0 mmol) in CH3CN (50 mL) was cooled in ice and treated in one portion with bromochloromethane (6.47 g, 50 mmol). The ice-bath was removed and the reaction mixture stirred at R.T. for 18 h. Then the solvent was evaporated and the crude product purified by chromatography on silica gel (eluted with CH2Cl2) to afford 1.27 g (77%) of the title compound, m.p.: 55°-57° C.

Workup

  1. customThe ice-bath was removed
  2. customThen the solvent was evaporated
  3. customthe crude product purified by chromatography on silica gel (eluted with CH2Cl2)

Sources & evidence

ORD record
ord-fe4db918087f4216b4a060603599d86d
Source dataset
uspto-grants-1992_05
Patent number
US05116833

Reaction notes

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