Cyclohexanol → HCID 21269282, compound

HRID 1194272Notes

Reaction equation

HRID 1194272 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH:6]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[CH:9]2)[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[O:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Na].[CH:34]1(O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C1(O)CCCCC1>CN(C)C=O>[CH3:1][C:2]1([CH3:20])[CH2:7][CH:6]([N:8]2[C:12]([C:13]([O:15][CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:14])=[CH:11][N:10]=[CH:9]2)[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 682631,1'-CarbonyldiimidazoleHCID 21269295HCID 21269295, compoundHCID 67903356HCID 67903356, compound

Product 1

HCID 21269282HCID 21269282, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.3 Parts of 1-(2,3-dihydro-2,2-dimethyl-4H-1-benzopyran-4-yl)-1H-imidazole-5-carboxylic acid were dissolved in 45 parts of warm N,N-dimethylformamide. After cooling to room temperature, 2 parts of 1,1'-carbonylbis[1H-imidazole] were added and the whole was stirred for 1 hour at this temperature. The whole was heated to ±80° C. and a mixture of 0.1 parts of a cyclohexanol sodium salt solution and 3 parts of cyclohexanol was added. After stirring for 5 days at ±80° C., the mixture was evaporated. The residue was taken up trichloromethane and water and the organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from hexane. The product was filtered off and dried, yielding 0.91 parts (20.5%) of cyclohexyl 1-(2,3-dihydro-2,2-dimethyl-4H-1-benzopyran-4-yl)-1H-imidazole-5-carboxylate; mp. 128.1° C. (compound 1.139).

Workup

  1. temperatureThe whole was heated
  2. customto ±80° C.
  3. additionwas added
  4. stirringAfter stirring for 5 days at ±80° C.
  5. customthe mixture was evaporated
  6. customthe organic layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from hexane
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-e16b43279cdd4559a1e30a0091b1dac7
Source dataset
uspto-grants-1989_03
Patent number
US04813998

Reaction notes

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