Hydrochloric Acid → HCID 13986129, compound

HRID 2232001Notes

Reaction equation

HRID 2232001 reaction equation
[CH:1]([N:3]([C:16](=[CH:22]O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:14][CH3:15])=O.Cl.C([NH2:27])=O>>[CH2:14]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[C:4]=1[N:3]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][N:27]=[CH:1]1)[CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 713FormamideHCID 72725881HCID 72725881, compound

Product 1

HCID 13986129HCID 13986129, compound

Procedure

1.3 g (3.9 mmol) of ethyl 2-(N-formyl-2-ethyl-6-trifluoromethylanilino)-3-hydroxyacrylate were heated for 4 hours at 150° C. with 20 ml of formamide and 5 ml of concentrated hydrochloric acid. After cooling, the mixture was extracted twice with diisopropyl ether, and the organic phase was washed with water, dried over sodium sulfate and evaporated. After chromatographic purification, 0.7 g (57% of theory) of ethyl 1-(2-ethyl-6-trifluoromethylphenyl)imidazole-5-carboxylate, a colorless oil, was obtained. The compound was identified by NMR spectroscopy.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted twice with diisopropyl ether
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customAfter chromatographic purification, 0.7 g (57% of theory) of ethyl 1-(2-ethyl-6-trifluoromethylphenyl)imidazole-5-carboxylate
  7. customa colorless oil, was obtained

Sources & evidence

ORD record
ord-b9736e333c1b4d3990972b183c5d8c89
Source dataset
uspto-grants-1988_11
Patent number
US04786312

Reaction notes

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