Water → Methyl 5-chloro-2-[(4-methylbenzene-1-sulfonyl)amino]benzoate

HRID 1356634Notes

Reaction equation

HRID 1356634 reaction equation
[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([NH2:12])=[CH:4][CH:3]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 78878Methyl 2-amino-5-chlorobenzoate

Product 1

HCID 18509325Methyl 5-chloro-2-[(4-methylbenzene-1-sulfonyl)amino]benzoateYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of methyl 5-chloroanthranilate (10.50 g (56.6 mmol) in pyridine (30 ml), p-toluenesulfonyl chloride (12.00 g (62.9 mmol)) was added with stirring at 5° C. The mixture was stirred at room temperature for 18 hours, and then, 200 ml of water was added to the resulting mixture. The crystals separated were filtered and washed to give 18.20 g (95%) of 4′-chloro-2′-methoxycarbonyl-p-toluenesulfonanilide as white crystals.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. customThe crystals separated
  3. filtrationwere filtered
  4. washwashed

Sources & evidence

ORD record
ord-884fb3447fa7495c865469151e7aff9c
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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