Bromochloromethane → 5-Chloromethylthio-1-methyltetrazole

HRID 249582

Reaction equation

HRID 249582 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-methyltetrazole

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-2dac4a8a25da4f5687e616cf7484f948
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Linked notes

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