Water → HCID 69521420, compound

HRID 856738Notes

Reaction equation

HRID 856738 reaction equation
[SH:1][C:2]1[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:25][CH2:26][S:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)(=O)=O)=CC=1.O>CN(C=O)C>[CH3:7][N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[S:1][CH2:25][CH2:26][S:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 86595196HCID 86595196, compoundHCID 178480602HCID 178480602, compound

Product 1

HCID 69521420HCID 69521420, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-mercapto-1-methylimidazole (0.81 g) was dissolved in DMF (16.2 ml), potassium carbonate (1.37 g) was added to the mixture, 2-[(4-nitrophenyl)thio]ethyl 4-methylbenzene sulfonate (3.0 g) was added to the mixture, and the mixture was stirred for 12 hours at 60° C. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was washed with hexane/ethyl acetate, to give 1-methyl-2-[[2-[(4-nitrophenyl)thio]ethyl]thio]imidazole (1.3 g).

Workup

  1. additionwas added to the mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-47cfb4ba96144f28b4161366e792647c
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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