Water → HCID 54265305, compound

HRID 622311Notes

Reaction equation

HRID 622311 reaction equation
[N+]([O-])(O)=O.[CH:5]1([CH:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]2[C:16]([C:17]([O:19]C)=[O:18])=[CH:15][N:14]=[CH:13]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[OH-].[Na+].O>C(O)(=O)C>[CH:21]1([CH:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:12]2[C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=[CH:13]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 67935419HCID 67935419, compound

Product 1

HCID 54265305HCID 54265305, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 8.7 parts of methyl 1-(cyclohexylphenylmethyl)-1H-imidazole-5-carboxylate mononitrate, 9 parts of a sodium hydroxide solution 50% and 45 parts of water was stirred for 1 hour at reflux temperature. 35 Parts of water were added. After cooling, the reaction mixture was neutralized with acetic acid. The product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of ethanol and acetonitrile. The product was filtered off (the filtrate was set aside) and dried in vacuo at 50° C., yielding a first fraction of 2.1 parts (30.8%) of 1-(cyclohexylphenylmethyl)-1H-imidazole-5-carboxylic acid; mp. 249.5° C. (compound 1.251).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionThe product was extracted with 1,1'-oxybisethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from a mixture of ethanol and acetonitrile
  8. filtrationThe product was filtered off (the filtrate
  9. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-6071e1c7c9914440bebc01b570d9785e
Source dataset
uspto-grants-1988_09
Patent number
US04770689

Reaction notes

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