Dichloromethane → HCID 58592599, compound

HRID 2222095Notes

Reaction equation

HRID 2222095 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:12])[C:7]([CH2:10][OH:11])=[N:8][CH:9]=1)=[O:4].[H-].[Na+].S(OC)(O[CH3:19])(=O)=O.ClCCl>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:12])[C:7]([CH2:10][O:11][CH3:19])=[N:8][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 59711806HCID 59711806, compound

Product 1

HCID 58592599HCID 58592599, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-hydroxymethyl-3-methyl-3H-imidazole-4-carboxylic acid methyl ester (250 mg, 1.5 mmol) in dimethylformamide (10 ml) is subsequently treated with sodium hydride (71 mg 60% dispersion in mineral oil, 1.8 mmol) and after 0.5 h with dimethyl sulfate (0.17 ml, 1.8 mmol). After 1 h at ambient temperature, the volatile componantes are removed in vacuo, the residue taken up in ethyl accetate (20 ml) and water (20 ml) and the phases separated. The aqueous phase is extracted twice with ethyl acetate (20 ml each) and the combined organic layers are dryed with magnesium sulfate and evaporated to dryness. Flash chromatography (silica, eluent dichloromethane containing 4% methanol) afforded the title compound as white crystals (42% yield). MS: m/e=185(M+H+), mp 74-77° C.

Workup

  1. customthe volatile componantes are removed in vacuo
  2. customthe phases separated
  3. extractionThe aqueous phase is extracted twice with ethyl acetate (20 ml each)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-ac3868a5a29041fc875af470e6071e26
Source dataset
uspto-grants-2008_05
Patent number
US07371749B2

Reaction notes

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