Water → HCID 54109521, compound

HRID 258700Notes

Reaction equation

HRID 258700 reaction equation
[H-].[Na+].[S:3]([C:7]1[NH:8][CH:9]=[CH:10][N:11]=1)([CH3:6])(=[O:5])=[O:4].Cl[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].O>CN(C)C=O.C(Cl)Cl>[S:3]([C:7]1[N:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][N:11]=1)([CH3:6])(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 993901H-Imidazole, 2-(methylsulfonyl)- (9CI)

Product 1

HCID 54109521HCID 54109521, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (50% suspension in mineral oil) (5.04 g.) is added, under a nitrogen atmosphere, to a solution of 2-mesyl-imidazole (15.3 g.) in dimethylformamide (130 cc.). Ethyl chloroacetate (12.9 g.) is then added. Reaction is allowed to take place for 20 hours, with stirring, at a temperature of about 20° C. The reaction mixture is then poured into water (4 liters) and extraction is effected using methylene chloride (1 liter). The methylene chloride extracts are washed with water, dried over sodium sulphate, treated with decolorising charcoal and then concentrated to dryness under reduced pressure (0.5 mm.Hg) to yield ethyl (2-mesyl-imidazol-1-yl)-acetate (21.4 g.) in the form of an oil.

Workup

  1. customReaction
  2. customfor 20 hours
  3. washThe methylene chloride extracts are washed with water
  4. dry with materialdried over sodium sulphate
  5. additiontreated with decolorising charcoal
  6. concentrationconcentrated to dryness under reduced pressure (0.5 mm.Hg)

Sources & evidence

ORD record
ord-8d03edfc897a427fbd339f239b7ac215
Source dataset
uspto-grants-1977_07
Patent number
US04034088

Reaction notes

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