5-Chloro-2-methoxybenzene-1-sulfonyl chloride → 3-(5-Chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-5-trifluoromethyl-benzoic acid methyl ester

HRID 1660829Notes

Reaction equation

HRID 1660829 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7]([OH:14])=[C:6]([NH2:15])[CH:5]=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([S:24](Cl)(=[O:26])=[O:25])[CH:23]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7]([OH:14])=[C:6]([NH:15][S:24]([C:22]2[CH:23]=[C:18]([Cl:17])[CH:19]=[CH:20][C:21]=2[O:28][CH3:29])(=[O:25])=[O:26])[CH:5]=1

Participants

4

Reactant 2

HCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chlorideHCID 667893973-Amino-4-hydroxy-5-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 667886743-(5-Chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-5-trifluoromethyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-amino-4-hydroxy-5-trifluoromethyl-benzoic acid methyl ester (4.66 g, 19.8 mmol) and 5-chloro-2-methoxybenzenesulfonyl chloride (4.78 g, 19.8 mmol) in toluene (38 mL) was heated at reflux for 48 h. After cooling, the precipitate was collected by filtration and washed with toluene to afford 3-(5-chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-5-trifluoromethyl-benzoic acid methyl ester. Off-white solid, MS (ISP)=438.0 (M−H)−.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. temperatureAfter cooling
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with toluene

Sources & evidence

ORD record
ord-ed296ae9e1314fc1a8963f7606fa720d
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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