Imidazole → Y-20811 free acid

HRID 543332노트

반응식

HRID 543332 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

HCID 121911Y-20811 free acid

시약·촉매·용매 3

HCID 23978Copper촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e49d30a617a648acbbab23208fc8fecd
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04661603

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