4-Aminobenzoic Acid → 4-[(4-Methylbenzene-1-sulfonyl)amino]benzoic acid

HRID 1957400Notes

Reaction equation

HRID 1957400 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].[NH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.S(Cl)(Cl)(=O)=O>C(OC(C)C)(C)C.O>[C:22]([C:21]1[CH:25]=[CH:26][C:18]([NH:17][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])=[CH:19][CH:20]=1)([OH:24])=[O:23]

Participants

7

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 73974-Toluenesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 5613854-[(4-Methylbenzene-1-sulfonyl)amino]benzoic acidYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of 190.5 g (1 mole) of 4-toluenesulfonyl chloride in 300 ml of i-propyl ether is added dropwise at 20°-30° C. to one of 252 g (3 mole) of sodium bicarbonate and 139.1 g (1 mole) of 4-aminobenzoic acid in 2.5 l of water. The mixture is stirred vigorously for 2-4 hours, until the sulfonyl chloride has been consumed. The aqueous solution is separated off and then adjusted to pH 1 with concentrated hydrochloric acid, and the precipitate is taken up in propyl acetate. The extract is washed 2× with 2N hydrochloric acid and 1× with water, dried over sodium sulfate and evaporated. 240 g (82.5% of theory) of N-(4-carboxyphenyl)-4-toluenesulfonamide are obtained.

Workup

  1. customhas been consumed
  2. customThe aqueous solution is separated off
  3. washThe extract is washed 2× with 2N hydrochloric acid and 1× with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9cb7d2fb7c2f4b2d9d6cd65dd11fb795
Source dataset
uspto-grants-1998_07
Patent number
US05783696

Reaction notes

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