Dimethyl Sulfate → HCID 14882462, compound

HRID 248768Notes

Reaction equation

HRID 248768 reaction equation
[H-].[Na+].[Cl:3][C:4]1[NH:5][C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1.S(OC)(O[CH3:24])(=O)=O>CN(C)C=O>[Cl:3][C:4]1[N:5]([CH3:24])[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 14882458HCID 14882458, compound

Product 1

HCID 14882462HCID 14882462, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.6 g of sodium hydride was added to a solution of 7 g (0.028 mol) of ethyl 2-chloro-4-phenylimidazole-5-carboxylate in 25 ml of dimethylformamide. Upon completion of gas evolution, 4.2 g (0.033 mol) of dimethyl sulfate was added and the mixture was heated at 80° C. for 11/2 hours. The dimethylformamide was removed under reduced pressure and the residue was poured into dilute ammonium hydroxide. After extraction with ethyl acetate, drying and removal of the solvent, chromatography on silica gel (developer: ethyl acetate/pentane) gave ethyl 2-chloro-1-methyl-4-phenylimidazole-5-carboxylate (compound no. 2.001) of m.p. 54° to 55° C.

Workup

  1. customThe dimethylformamide was removed under reduced pressure
  2. additionthe residue was poured into dilute ammonium hydroxide
  3. extractionAfter extraction with ethyl acetate
  4. customdrying
  5. customremoval of the solvent, chromatography on silica gel (developer: ethyl acetate/pentane)

Sources & evidence

ORD record
ord-a3e2741b36204b9c9d6a3fcbdae9deff
Source dataset
uspto-grants-1993_05
Patent number
US05211737

Reaction notes

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