Imidazole → Y-20811 free acid

HRID 543332Notes

Reaction equation

HRID 543332 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[CH:12]([C:14]1[CH:19]=[C:18](I)[CH:17]=[CH:16][C:15]=1[CH3:21])[OH:13].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(=O)([O-])[O-].[K+].[K+].[F-].[K+].O.O.O.[S-2].[Na+].[Na+]>[Cu].O.CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[CH:12]([C:14]1[CH:19]=[C:18]([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)[CH:17]=[CH:16][C:15]=1[CH3:21])[OH:13]

Participants

9

Reactant 5

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 522689Potassium FluorideHCID 20206231alpha-(2,6-Dimethyl-4-carboxyphenyl)-2-methyl-5-iodobenzenemethanolHCID 24846073Sodium sulphide trihydrate

Product 1

HCID 121911Y-20811 free acid

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension 19.8 g of α-(2,6-dimethyl-4-carboxyphenyl)-2-methyl-5-iodobenzenemethanol, 5.1 g of imidazole, 13.8 g of potassium carbonate and 120 ml of dimethylformamide are added 0.4 g of potassium fluoride and 0.4 g of copper powder, and the mixture is stirred at 135°-140° C. for 30 hours. After cooling, to the reaction mixture is added 240 ml of water and further 0.45 g of sodium sulfide trihydrate. The whole mixture is stirred for 30 minutes. The precipitated copper sulfide is filtered with sellaite under reduced pressure and the filtrate is adjusted to pH 4 with concentrated hydrochloric acid under heating and stirring. The precipitated crystals are collected by filtration, washed with water and dried. Recrystallization from dimethylformamide gives α-(2,6-dimethyl-4-carboxyphenyl)-2-methyl-5-(1-imidazolyl)benzenemethanol, melting at 309°-311° C. with decomposition in high yield.

Workup

  1. temperatureAfter cooling, to the reaction mixture
  2. stirringThe whole mixture is stirred for 30 minutes
  3. filtrationThe precipitated copper sulfide is filtered with sellaite under reduced pressure
  4. temperatureunder heating
  5. stirringstirring
  6. filtrationThe precipitated crystals are collected by filtration
  7. washwashed with water
  8. customdried
  9. customRecrystallization from dimethylformamide

Sources & evidence

ORD record
ord-e49d30a617a648acbbab23208fc8fecd
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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