Triethylamine → HCID 178504999, compound

HRID 437768Notes

Reaction equation

HRID 437768 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>CC(C)=O>[CH3:24][S:25]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[CH:4][CH:3]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride3×HCID 178507443HCID 178507443, compound

Product 1

HCID 178504999HCID 178504999, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(p-aminophenyl)-4-trifluoromethylimidazole (3.0 g.) in acetone (50 ml.) and triethylamine (2.7 g.) is added methanesulfonyl chloride (1.5 g.). After refluxing for four hours, a second portion of methanesulfonyl chloride (1.5 g.) is added. Reflux is continued 20 hours, a third portion of methanesulfonyl chloride (1.5 g.) is added and reflux continued another four hours. The reaction mixture is filtered and concentrated to an oil which, upon trituration with water, affords a solid. After chromatography on silica gel and recrystallization from a mixture of acetonitrile and water 1.3 g. of 2-(p-methylsulfonamidophenyl)-4-trifluoromethylimidazole, m.p. 253°-255° C. is obtained.

Workup

  1. temperatureAfter refluxing for four hours
  2. temperatureReflux
  3. temperaturereflux
  4. waitcontinued another four hours
  5. filtrationThe reaction mixture is filtered
  6. concentrationconcentrated to an oil which, upon trituration with water
  7. customaffords a solid
  8. customAfter chromatography on silica gel and recrystallization
  9. additionfrom a mixture of acetonitrile and water 1.3 g

Sources & evidence

ORD record
ord-b68f907f4d1748f7a204c6f83f0154c6
Source dataset
uspto-grants-1977_06
Patent number
US04032522

Reaction notes

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