3,5-Bis(trifluoromethyl)benzenesulphonyl chloride → Benzhydrol 2-[2-[3,5-bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzoate

HRID 1077973Notes

Reaction equation

HRID 1077973 reaction equation
[CH:1]([OH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:17]=1[O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([O-:23])=[O:22].[F:36][C:37]([F:53])([F:52])[C:38]1[CH:39]=[C:40]([S:48](Cl)(=[O:50])=[O:49])[CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1>N1C=CC=CC=1>[CH:1]([OH:14])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:47][C:44]([F:45])([F:46])[C:42]1[CH:41]=[C:40]([S:48]([NH:15][C:16]2[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[CH:28][C:17]=2[O:18][C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21]([O-:23])=[O:22])(=[O:49])=[O:50])[CH:39]=[C:38]([C:37]([F:53])([F:52])[F:36])[CH:43]=1

Participants

4

Reactant 2

HCID 5209453,5-Bis(trifluoromethyl)benzenesulphonyl chlorideHCID 131719119Benzhydrol 2-(2-amino-4-trifluoromethylphenoxy)benzoate

Product 1

HCID 131719489Benzhydrol 2-[2-[3,5-bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzhydrol 2-(2-amino-4-trifluoromethylphenoxy)benzoate (4 g, 8.6 mmol) was dissolved in pyridine (25 mL) and stirred under argon at room temperature. 3,5-bis(trifluoromethyl)benzenesulfonyl chloride (4.05 g, 12.9 mmol) was added in portions, and the mixture stirred for 16 h. The solvent was evaporated, and the residue was purified by flash chromatography (silica gel, ethyl acetate/hexane) to give the title compound as a white solid. 1H NMR (250 MHz, CDCl3) δ8.25 (br s, 1H), 8.15 (s, 2H), 7.99 (dd, 1H), 7.85-7.92 (m, 2H), 7.1-7.5 (m, 13H), 7.01 (s, 1H), 6.72 (d, 1H), 6.45 (dd, 1H).

Workup

  1. stirringthe mixture stirred for 16 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e3955088cf2c4b68885f362426fafb5f
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

Loading…