Triethylamine → HCID 178504999, compound

HRID 1703763Notes

Reaction equation

HRID 1703763 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 4 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 4 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 4 hours
  2. temperatureReflux
  3. temperaturereflux
  4. waitcontinued another 4 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-2bb1ec72636b401387b41957c09da75f
Source dataset
uspto-grants-1978_11
Patent number
US04125530

Reaction notes

Loading…