Imidazole → alpha-(2,6-Dimethyl-4-carboxyphenyl)-2-chloro-5-(1-imidazolyl)benzenemethanol

HRID 543334Notes

Reaction equation

HRID 543334 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[Cl: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[Cl:21])[OH:13]

Participants

9

Reactant 5

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 522689Potassium FluorideHCID 13851128alpha-(2,6-Dimethyl-4-carboxyphenyl)-2-chloro-5-iodobenzenemethanolHCID 24846073Sodium sulphide trihydrate

Product 1

HCID 13851129alpha-(2,6-Dimethyl-4-carboxyphenyl)-2-chloro-5-(1-imidazolyl)benzenemethanol

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 21 g of α-(2,6-dimethyl-4-carboxyphenyl)-2-chloro-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 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 then dried. Recrystallization from dimethylformamide gives α-(2,6-dimethyl-4-carboxyphenyl)-2-chloro-5-(1-imidazolyl)benzenemethanol, melting at 318°-320° C. with decomposition, as white crystals 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-4cfb6f9927cd416f9b2d10b9a7800b8a
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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