4-Amino-2-chlorophenol → 2-Chloro-N-(3-chloro-4-hydroxy-phenyl)-4-trifluoromethylbenzenesulfonamide

HRID 1819808Notes

Reaction equation

HRID 1819808 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.[Cl:10][C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:12]=1[S:21](Cl)(=[O:23])=[O:22]>>[Cl:10][C:11]1[CH:16]=[C:15]([C:17]([F:19])([F:18])[F:20])[CH:14]=[CH:13][C:12]=1[S:21]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1)(=[O:23])=[O:22]

Participants

3

Reactant 2

HCID 775784-Amino-2-chlorophenolHCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 185115302-Chloro-N-(3-chloro-4-hydroxy-phenyl)-4-trifluoromethylbenzenesulfonamide

Procedure

2-Chloro-N-(3-chloro-4-hydroxy-phenyl)-4-trifluoromethyl-benzenesulfonamide was synthesized (92%) from 4-amino-2-chlorophenol (Aldrich) and 2-chloro-4-trifluoromethylbenzenesulfonyl chloride in a similar manner as described in Example 421. 1H NMR (400 MHz, DMSO-d6) δ 10.57 (s, 1H), 10.17 (s, 1H), 8.14 (d, J 1.0 Hz, 1H), 8.12 (d, J=8.3 Hz, 1H), 7.88 (dd, J=8.5, 1.4 Hz, 1H), 7.04 (d, J=2.5 Hz, 1H), 6.88 (dd, J=8.7, 2.5 Hz, 1H), 6.82 (d, J=8.7 Hz, 1H). MS (EI): m/z 384 (M+H).

Sources & evidence

ORD record
ord-166addac41ab486a8116cf2bebcb4c18
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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