Imidazole → HCID 13073178, 화합물

HRID 223462노트

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HRID 223462 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([S:20]([C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])(=[O:22])=[O:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[N+:29]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1)([O-:31])=[O:30].C(=O)([O-])[O-].[K+].[K+].N1C=CN=C1>C(Cl)Cl.C1(C)C=CC=CC=1.O.CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([S:20]([C:23]([F:28])([F:27])[CH:24]([F:25])[F:26])(=[O:21])=[O:22])[N:11]([CH2:36][C:35]3[CH:38]=[CH:39][C:32]([N+:29]([O-:31])=[O:30])=[CH:33][CH:34]=3)[C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

참가 물질

9

반응물 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 44188Tiflamizole2회HCID 660114-Nitrobenzyl bromide

생성물 1

HCID 13073178HCID 13073178, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
75 °C

실험 절차

4.20 g (0.01 mole) of 4,5-bis-(4-fluorophenyl)-2-[(1,1,2,2-tetrafluoroethyl)sulfonyl]-1H-imidazole, prepared according to the method described in U.S. Pat. No. 4,190,666, 2.7 g (0.0125 mole) of 4-nitrobenzylbromide, 1.73 g (0.0125 mole) of anhydrous powdered potassium carbonate, and 50 ml of dimethylformamide were combined in a round bottom flask and stirred and heated under nitrogen in an oil bath at 75° C. for 20 hours. The reaction mixture was cooled to room temperature and poured into 500 ml of water. The product was extracted with methylene chloride. The methylene chloride solution was washed several times with water to remove dimethylformamide, dried over sodium sulfate, filtered, and evaporated on a rotary evaporator. The remaining oil was triturated with ether, which caused the product to crystallize. The white solid was filtered, washed with ether, and dried to yield 4.9 g, m.p. 169°-170°. The product was freed from a small amount, usually less than 1% of 4,5-bis-(4-fluorophenyl)-2-[ (1,1,2,2-tetrafluoroethyl)sulfonyl]-1H-imidazole by dissolving it in a small amount of methylene chloride and putting the solution through a preparative liquid chromatography apparatus using toluene to elute. After evaporating the toluene from the main fraction on a rotary evaporator, 4.4 g of product, m.p. 176°-177° was obtained. A mass spectrum of the product showed it to have a m/e of 555.4 and also showed it to contain no measurable starting imidazole, m/e 420.3.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted with methylene chloride
  3. washThe methylene chloride solution was washed several times with water
  4. customto remove dimethylformamide
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated on a rotary evaporator
  8. customThe remaining oil was triturated with ether, which
  9. customto crystallize
  10. filtrationThe white solid was filtered
  11. washwashed with ether
  12. customdried
  13. customto yield 4.9 g, m.p. 169°-170°
  14. washto elute
  15. customAfter evaporating the toluene from the main fraction
  16. customon a rotary evaporator, 4.4 g of product
  17. customm.p. 176°-177° was obtained

출처 및 근거

ORD 기록
ord-b9db029a45d3477ab213869db0ed39b8
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04355041

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