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

HRID 220775Notes

Reaction equation

HRID 220775 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(N(CC)CC)C.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>ClCCl.CCOC(C)=O>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8635Methyl Anthranilate

Product 1

HCID 7376052-(Toluene-4-sulfonylamino)-benzoic acid methyl esterYield 81.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methyl anthranilate (110 g, 0.73 mol) was dissolved in dichloromethane (1 liter) at 0° C. and triethylamine (115 ml, 0.8 mol) was added. Tosyl chloride (133 g, 0.745 mol) was added portionwise at 0° C. The reaction mixture was stirred for 30 min at 0° C. and 64 h at room temperature. The mixture was reduced in vacuo. The residue was dissolved in EtOAc and the organic layer was washed with 5% KHCO3 (aq) solution, 1N HCl solution and brine, dried, filtered and concentrated in vacuo. The residue was crystallised from EtOAc/hexane to yield the title compound (181 g, 81%).

Workup

  1. washthe organic layer was washed with 5% KHCO3 (aq) solution, 1N HCl solution and brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallised from EtOAc/hexane

Sources & evidence

ORD record
ord-2a268bc4cae14f43b04fcc80f104cada
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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