Formaldehyde → HCID 59711806, compound

HRID 2222094Notes

Reaction equation

HRID 2222094 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:10])[CH:7]=[N:8][CH:9]=1)=[O:4].[CH2:11]=[O:12].ClCCl>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:10])[C:7]([CH2:11][OH:12])=[N:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 2736896METHYL 1-METHYL-1H-IMIDAZOLE-5-CARBOXYLATE

Product 1

HCID 59711806HCID 59711806, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
135 °C

Procedure

A suspension of 3-methyl-3H-imidazole-4-carboxylic acid methyl ester (4.0 g, 29 mmol) and paraformaldehyde (18 g, corresponding to 570 mmol) in methanol (40 ml) was heated in a sealed vessel to 135° C. for 60 h. After cooling to ambient temperature, the solution was evaporated to dryness. Flash chromatography (silica, eluent dichloromethane containing 5% methanol) afforded the title compound as white crystals (56% yield). MS: m/e=171(M+H+), mp 145-147° C.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-6426b833a56f4f979a3b200dcc32dd28
Source dataset
uspto-grants-2008_05
Patent number
US07371749B2

Reaction notes

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