3,5-Bis(trifluoromethyl)benzenesulphonyl chloride → Benzhydrol 2-[2-[3,5-Bis(trifluoromethyl)phenyl]sulfonamido-4-trifluoromethylphenoxy]-4-methoxybenzoic acid

HRID 1077988Notes

Reaction equation

HRID 1077988 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:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:17]=1[O:18][C:19]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:20]=1[C:21]([O-:23])=[O:22].[F:38][C:39]([F:55])([F:54])[C:40]1[CH:41]=[C:42]([S:50](Cl)(=[O:52])=[O:51])[CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1>N1C=CC=CC=1>[F:49][C:46]([F:47])([F:48])[C:44]1[CH:43]=[C:42]([S:50]([NH:15][C:16]2[CH:33]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:31]=[CH:30][C:17]=2[O:18][C:19]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:20]=2[C:21]([OH:23])=[O:22])(=[O:51])=[O:52])[CH:41]=[C:40]([C:39]([F:55])([F:54])[F:38])[CH:45]=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

Participants

4

Reactant 2

HCID 5209453,5-Bis(trifluoromethyl)benzenesulphonyl chlorideHCID 86749720Benzhydrol 2-(2-amino-4-trifluoromethylphenoxy)-4-methoxybenzoate

Product 1

HCID 19430590Benzhydrol 2-[2-[3,5-Bis(trifluoromethyl)phenyl]sulfonamido-4-trifluoromethylphenoxy]-4-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzhydrol-2-(2-amino-4-trifluoromethylphenoxy)-4-methoxybenzoate (950 mg, 0.0019 mol) and 3,5-bis(trifluoromethyl)benzenesulfonyl chloride (2.4 g, 0.008 mol) were mixed in pyridine, under argon, at room temperature for 16 h. The solvent was evaporated and the residue flash chromatographed (silica gel, ethyl acetate/hexane) to yield the title compound. 1H NMR (250 MHz, CDCl3) δ8.11 (s, 1H), 7.86-7.98 (m, 2H), 7.08-7.32 (s, 10 H), 6.94 (s, 1H), 6.87 (d, 1H), 6.70 (q, 3H), 6.48 (d, 1H), 6.11 (d, 1H), 3.73 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue flash chromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-762864d3193c43f0832ee6e358242d0b
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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