Bromochloromethane → HCID 10241417, compound

HRID 1707425Notes

Reaction equation

HRID 1707425 reaction equation
[CH3:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.[H-].[Na+].Br[CH2:11][Cl:12]>CN(C)C=O.O>[Cl:12][CH2:11][S:7][C:4]1[S:3][C:2]([CH3:1])=[N:6][N:5]=1

Participants

6

Reactant 3

HCID 6333BromochloromethaneHCID 24758Sodium hydrideHCID 178434161HCID 178434161, compound

Product 1

HCID 10241417HCID 10241417, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-1,3,4-thiadiazole-5-thiol (2.64 g: 20 mMol.) in dimethylformamide (40 ml) is added under ice cooling sodium hydride (880 mg: 60% dispersion in oil: 1.1 equivalents: 22 mMol.) in portions, and the mixture is stirred for 10 minutes. To the resulting solution is added bromochloromethane (40 ml), and the mixture is stirred at the same temperature for another 1 hour and 30 minutes. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and purified by silica gel chromatography (toluene: ethyl acetate=10:1) to give 5-chloromethylthio-2-methyl-1,3,4-thiadiazole (3.3 g) as colorless oil. Yield: 91%.

Workup

  1. stirringthe mixture is stirred at the same temperature for another 1 hour and 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over sodium sulfate
  5. custompurified by silica gel chromatography (toluene: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d299abff6f2746e69a7afaacca0ae425
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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