Ethyl chloroacetate → HCID 53940535, compound

HRID 258696Notes

Reaction equation

HRID 258696 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[NH:6][CH:7]=[CH:8][N:9]=1.Cl[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>CN(C)C=O>[CH3:3][S:4][C:5]1[N:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 1346522-(Methylsulfanyl)-1H-imidazole

Product 1

HCID 53940535HCID 53940535, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (4.22 g.) (50% suspension in mineral oil) is added, under a nitrogen atmosphere, to a solution of 2-methylthio-imidazole (10 g.) in dimethylformamide (100 cc.). Ethyl chloroacetate (10.8 g.) is then added and reacted for 20 hours, with stirring, at a temperature of about 20° C. The mixture is concentrated to dryness under reduced pressure (20 mm.Hg), the residue is taken up in water (1.8 liters) and the aqueous solution is extracted with methylene chloride (560 cc.). The methylene chloride extracts are washed with water, dried over sodium sulphate, treated with decolorising charcoal and concentrated to dryness under reduced pressure (20 mm.Hg) to give ethyl (2-methylthio-imidazol-1-yl)-acetate (14.5 g.) in the form of an oil.

Workup

  1. customreacted for 20 hours
  2. concentrationThe mixture is concentrated to dryness under reduced pressure (20 mm.Hg)
  3. extractionthe aqueous solution is extracted with methylene chloride (560 cc.)
  4. washThe methylene chloride extracts are washed with water
  5. dry with materialdried over sodium sulphate
  6. additiontreated with decolorising charcoal
  7. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)

Sources & evidence

ORD record
ord-63928b1d3f3d41798ea3e6ea4dcbde97
Source dataset
uspto-grants-1977_07
Patent number
US04034088

Reaction notes

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