Bromochloromethane → 5-Chloromethylthio-1-methyltetrazole

HRID 1707426Notes

Reaction equation

HRID 1707426 reaction equation
[Na].[CH3:2][N:3]1[C:7]([SH:8])=[N:6][N:5]=[N:4]1.Br[CH2:10][Cl:11]>CN(C)C=O.O>[Cl:11][CH2:10][S:8][C:7]1[N:3]([CH3:2])[N:4]=[N:5][N:6]=1

Participants

5

Reactant 2

HCID 6333BromochloromethaneHCID 178482029HCID 178482029, compound

Product 1

HCID 103520355-Chloromethylthio-1-methyltetrazoleYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyltetrazole-5-thiol sodium salt (2.00 g: 14.5 mMol.) in dimethylformamide (20 ml) under ice cooling is added bromochloromethane (20 ml) in one portion, and the mixture is stirred for 1.5 hour. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue is purified by silica gel column chromatography (toluene: ethyl acetate=20:1-10:1) to give 5-chloromethylthio-1-methyltetrazole as colorless crystals (1.73 g). Yield: 72%. m.p. 55° to 56° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column chromatography (toluene: ethyl acetate=20:1-10:1)

Sources & evidence

ORD record
ord-aa17aa978c944620a9aa9094d688940a
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

Loading…