Sodium hydride → HCID 21493029, compound

HRID 1973151Notes

Reaction equation

HRID 1973151 reaction equation
[SH:1][C:2]1[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=1.[H-].[Na+].[CH3:10][N:11]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]1S(C)(=O)=O>CN(C)C=O>[CH3:7][N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[S:1][C:12]1[N:11]([CH3:10])[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 100595SulfonidazoleHCID 178480602HCID 178480602, compound

Product 1

HCID 21493029HCID 21493029, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 11.4 g of 2-mercapto-1-methyl-imidazole in 60 ml of dimethylformamide is added dropwise over the course of 15 minutes to a suspension of 4.8 g of 50% strength sodium hydride in 100 ml of dimethylformamide at 20° to 30° C, whilst stirring. The resulting solution is then added dropwise over the course of 30 minutes to a solution of 20.5 g of 1-methyl-2-methylsulphonyl-5-nitro-imidazole in 80 ml of dimethylformamide at 20° to 30° C whilst stirring. Thereafter the reaction mixture is stirred for a further hour at 100° C and is evaporated. The evaporation residue is extracted by shaking with 200 ml of methylene chloride and 200 ml of water and the methylene chloride extract is separated off, washed with 50 ml of water, dried over anhydrous magnesium sulphate and evaporated. After two recrystallisations from ethyl acetate the evaporation residue yields pure 1-methyl-2-[(1-methyl-5-nitro-2-imidazolyl)mercapto]-imidazole of melting point 123°-124° C.

Workup

  1. stirringwhilst stirring
  2. stirringThereafter the reaction mixture is stirred for a further hour at 100° C
  3. customis evaporated
  4. extractionThe evaporation residue is extracted
  5. stirringby shaking with 200 ml of methylene chloride and 200 ml of water
  6. extractionthe methylene chloride extract
  7. customis separated off
  8. washwashed with 50 ml of water
  9. dry with materialdried over anhydrous magnesium sulphate
  10. customevaporated
  11. customAfter two recrystallisations from ethyl acetate the evaporation residue

Sources & evidence

ORD record
ord-f6bff940e7cc48ac90a5698992391f7d
Source dataset
uspto-grants-1976_12
Patent number
US03996238

Reaction notes

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