Imidazole → HCID 13073178, compound

HRID 223462Notes

Reaction equation

HRID 223462 reaction equation
[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

Participants

9

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 44188Tiflamizole2×HCID 660114-Nitrobenzyl bromide

Product 1

HCID 13073178HCID 13073178, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b9db029a45d3477ab213869db0ed39b8
Source dataset
uspto-grants-1982_10
Patent number
US04355041

Reaction notes

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