Ammonia → Ethyl 4-methyl-5-imidazolcarboxylate

HRID 1065118Notes

Reaction equation

HRID 1065118 reaction equation
Cl.C=O.O[N:5]=[C:6](C(C)=O)C(OCC)=O.[C:15]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:16][C:17]([CH3:19])=O.[NH3:24]>>[CH3:19][C:17]1[NH:5][CH:6]=[N:24][C:16]=1[C:15]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 5

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8868Ethyl AcetoacetateHCID 178472877HCID 178472877, compound

Product 1

HCID 99200Ethyl 4-methyl-5-imidazolcarboxylateYield 61%

Procedure

To a stirred cold (0°) suspension of concentrated hydrochloric acid (516 ml.) and paraformaldehyde (105 g.) was added ethyl 2-hydroxyiminoacetoacetate prepared from 130 g. (1 m.) of ethyl acetoacetate over two hours maintaining the reaction temperature at 5°-15°. After stirring one hour at 5°-15°, aqueous ammonia (28%) was added slowly until pH reached 5 and temperature rose to 70° over 35 minutes. The reaction mixture was held at pH 5 at 65°-70° for 30 minutes and then aqueous ammonia (28%) was added until the mixture was neutral. The mixture was cooled to 10° and the solid material was filtered off and washed with water and isopropanol and dried to give ethyl 5-methyl-4-imidazolecarboxylate, m.p. 204°-206°, yield 61-65%.

Workup

  1. customprepared from 130 g
  2. waitrose to 70° over 35 minutes
  3. waitThe reaction mixture was held at pH 5 at 65°-70° for 30 minutes
  4. temperatureThe mixture was cooled to 10°
  5. filtrationthe solid material was filtered off
  6. washwashed with water and isopropanol
  7. customdried

Sources & evidence

ORD record
ord-f3c0cdf6fc32413abaee48fd2841c3c5
Source dataset
uspto-grants-1982_05
Patent number
US04328349

Reaction notes

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