4-Chlorobenzenesulfonyl chloride → 2-{[(4-Chlorophenyl)sulfonyl]amino}-4,5-dimethoxybenzoic acid

HRID 2053365Notes

Reaction equation

HRID 2053365 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:7][C:8]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 797364,5-Dimethoxyanthranilic acid

Product 1

HCID 12399912-{[(4-Chlorophenyl)sulfonyl]amino}-4,5-dimethoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

33.71 g (0.32 mol) of sodium carbonate were dissolved in 250 ml of water and warmed to 60° C. 25.00 g (0.13 mol) of 2-amino-4,5-dimethoxy-benzoic acid were introduced into the solution, and to this solution 29.55 g (0.14 mol) of 4-chloro-benzenesulfonyl chloride were added portionwise over 15 min. After cooling the mixture was filtered with suction, the residue was taken up in 1% sodium hydrogencarbonate solution, the solution filtered, and the product precipitated by addition of 1 N hydrochloric acid. 25.90 g (55%) of 2-(4-chloro-phenylsulfonylamino)-4,5-dimethoxy-benzoic acid of melting point (m.p.) 212-214° C. were obtained.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered with suction
  3. filtrationthe solution filtered
  4. customthe product precipitated by addition of 1 N hydrochloric acid
  5. custompoint (m.p.) 212-214° C.
  6. customwere obtained

Sources & evidence

ORD record
ord-cea54df742a341dd881e0bef014088a4
Source dataset
uspto-grants-2008_02
Patent number
US07326789B2

Reaction notes

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