Hydrochloric Acid → 4-Chloro-2-[4-chloro-3-(trifluoromethyl)benzenesulfonamido]benzoic acid

HRID 1898253Notes

Reaction equation

HRID 1898253 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[NH2:7][C:8]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][C:20]=1[C:29]([F:32])([F:31])[F:30].Cl>O.O1CCOCC1>[Cl:17][C:15]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([NH:7][S:25]([C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[C:20]([C:29]([F:32])([F:30])[F:31])[CH:21]=2)(=[O:27])=[O:26])[CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 666462-Amino-4-chlorobenzoic acidHCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl Chloride

Product 1

HCID 21286784-Chloro-2-[4-chloro-3-(trifluoromethyl)benzenesulfonamido]benzoic acidYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Na2CO3 (11.7 g, 110.7 mmol) in water (50 mL) and 1,4-dioxane (50 mL) at 60° C. was added 2-amino-4-chloro-benzoic acid (5.0 g, 29.14 mmol) followed by 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride (20.15 g, 72.48 mmol) in 3 portions and heated the resulting reaction mixture at 80° C. for 4 h. 2N HCl Was added until the reaction mixture became acidic (pH=˜2) and obtained white solid was filtered, washed with water, dried under high vacuum to obtain title compound (7.8 g) in 65% yield. MS (ES) M+Na expected 436.0. found 435.8.

Workup

  1. temperatureheated
  2. customthe resulting reaction mixture at 80° C. for 4 h
  3. customobtained white solid
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-5ab92b3e8795462297639db7de132db1
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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