Ammonia → Ethyl 4-methyl-5-imidazolcarboxylate

HRID 1065119Notes

Reaction equation

HRID 1065119 reaction equation
O[N:2]=[C:3](C(C)=O)C(OCC)=O.[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=O.S(=O)(=O)(O)O.C=O.[NH3:28]>>[CH3:16][C:14]1[NH:2][CH:3]=[N:28][C:13]=1[C:12]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 5

HCID 222Ammonia2×HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 8868Ethyl AcetoacetateHCID 178472877HCID 178472877, compound

Product 1

HCID 99200Ethyl 4-methyl-5-imidazolcarboxylateYield 50%

Procedure

One mole of ethyl 2-hydroxyimino-acetoacetate, prepared from 130 g. (1 m.) of ethyl acetoacetate, was added over 75 minutes to a stirred suspension of 166 ml. (3 m.) of concentrated sulfuric acid and 105 g. (3.5 m.) of paraformaldehyde at 5°-10°. The mixture was stirred at 5°-10° for four hours and aqueous ammonia (28%) was added to pH 5 and the temperature rose to 70°. The reaction mixture was held for 30 minutes at pH 5 at 65°-70° and then neutralized with aqueous ammonia (28%). The mixture was cooled to 10°. The solid material was filtered off, washed with water and isopropanol and dried to give ethyl 5-methyl-4-imidazolecarboxylate (yield 50%).

Workup

  1. customat 5°-10°
  2. customrose to 70°
  3. waitThe reaction mixture was held for 30 minutes at pH 5 at 65°-70°
  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-b5f6a855ddf847ee8e7729b7e08df088
Source dataset
uspto-grants-1982_05
Patent number
US04328349

Reaction notes

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