4-Toluenesulfonyl chloride → 2-(Toluene-4-sulfonylamino)-benzoic acid methyl ester

HRID 2353856Notes

Reaction equation

HRID 2353856 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 8635Methyl Anthranilate

Product 1

HCID 7376052-(Toluene-4-sulfonylamino)-benzoic acid methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 2-Amino-benzoic acid methyl ester (900 g, 6 mol) in pyridine (6 L) was added p-Toluenesulfonyl chloride (1500 g, 7.5 mol). The mixture was stirred overnight at room temperature. The mixture was poured into ice water, and the resultant precipitates were collected by filtration. The filtrates were dissolved in CH2Cl2, and the solution washed with diluted HCl, H2O, and dried over MgSO4. The residue thus obtained was crystallized from ethanol to give 2-(Toluene-4-sulfonylamino)-benzoic acid methyl ester (1454 g, 80%).

Workup

  1. customthe resultant precipitates
  2. filtrationwere collected by filtration
  3. dissolutionThe filtrates were dissolved in CH2Cl2
  4. washthe solution washed with diluted HCl, H2O
  5. dry with materialdried over MgSO4
  6. customThe residue thus obtained
  7. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-3ee3e4d90a16473ba4e352c32e8c6fab
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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