Hydrochloric Acid → HCID 13752735, compound

HRID 1253125Notes

Reaction equation

HRID 1253125 reaction equation
[CH:1]([N:3]([CH:12]1[CH:17]([CH2:18][CH3:19])[CH2:16][CH2:15][CH2:14][CH:13]1[CH2:20][CH3:21])[C:4](=[CH:10]O)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=O.Cl.C([NH2:25])=O>>[CH2:20]([CH:13]1[CH2:14][CH2:15][CH2:16][CH:17]([CH2:18][CH3:19])[CH:12]1[N:3]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][N:25]=[CH:1]1)[CH3:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 713FormamideHCID 73187091HCID 73187091, compound

Product 1

HCID 13752735HCID 13752735, compoundYield 55%

Procedure

39.7 g (0.13 mol) of ethyl 2-(N-formyl-2,6-diethylcyclohexylamino)-3-hydroxy-acrylate, together with 240 ml of formamide and 24 ml of concentrated hydrochloric acid, were heated at 150° C. for 6 hours. After cooling, the mixture was extracted twice with diisopropyl ether, the organic phase was washed twice with water, dried over sodium sulfate and evaporated, and the residue was chromatographed over a silica gel column (mobile phase 7:3 petroleum ether (low-boiling)/ethyl acetate). 20.5 g (55% of theory) of ethyl 1-(2,6-diethylcyclohexyl)-imidazole-5-carboxylate was obtained as a colorless oil. Identification was effected by means of NMR spectroscopy.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted twice with diisopropyl ether
  3. washthe organic phase was washed twice with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customthe residue was chromatographed over a silica gel column (mobile phase 7:3 petroleum ether (low-boiling)/ethyl acetate)

Sources & evidence

ORD record
ord-7216c1bb6dc94da5bbeb8922ffc68fe4
Source dataset
uspto-grants-1988_05
Patent number
US04747868

Reaction notes

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