N-(4-bromophenyl)-1,1,1-trifluoromethanesulfonamide → HCID 69993988, compound

HRID 963429Notes

Reaction equation

HRID 963429 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])O[CH2:18][CH3:19]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:18][CH3:19])[S:9]([C:12]([F:15])([F:13])[F:14])(=[O:11])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 2133889N-(4-bromophenyl)-1,1,1-trifluoromethanesulfonamideHCID 53630039Ethylorthoformate

Product 1

HCID 69993988HCID 69993988, compoundYield 93%

Procedure

A solution of 1.52 g (5 mmol) of N-(4-bromophenyl)-C,C,C-trifluoro-methanesulphonamide (Example 13bv)) in 25 ml of ethyl orthoformate was heated to reflux for 6 hours. Subsequently, the readily volatile constituents were distilled off on a water-jet vacuum and the residue was chromatographed over a flash column with hexane/ethyl acetate 95:5. There were obtained 1.55 g (93%) of N-(4-bromophenyl)-N-ethyl-C,C,C- trifluoro-methanesulphonamide as a pale yellow oil. MS (EI): 331 and 333 (M+, 44%), 198 and 200 ([M-SO2 CF3 ]+, 80%), 118 ([M-(SO2CF3 +HBr)]+, 100%).

Workup

  1. temperatureto reflux for 6 hours
  2. distillationSubsequently, the readily volatile constituents were distilled off on a water-jet vacuum
  3. customthe residue was chromatographed over a flash column with hexane/ethyl acetate 95:5

Sources & evidence

ORD record
ord-6d2ffc1f0a2c484785c08db57ee1fd57
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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