Water → Methyl 4-(2-phenylsulfonylamino-5-chlorophenylaminocarbonyl)benzoate

HRID 1006536Notes

Reaction equation

HRID 1006536 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:12]=2[NH2:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:25][O:26][C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)=[O:28].O>C(Cl)Cl>[C:1]1([S:7]([NH:10][C:11]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:12]=2[NH:13][C:33]([C:32]2[CH:36]=[CH:37][C:29]([C:27]([O:26][CH3:25])=[O:28])=[CH:30][CH:31]=2)=[O:34])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 130413992-Phenylsulfonylamino-5-chloroaniline

Product 1

HCID 12017672Methyl 4-(2-phenylsulfonylamino-5-chlorophenylaminocarbonyl)benzoateYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylsulfonylamino-5-chloroaniline (90 mg; prepared in Reference Example 12.) and pyridine (0.05 ml) in methylene chloride (5 ml), 4-methoxycarbonylbenzoic acid chloride (70 mg) was added at room temperature in a stream of argon. The mixture was stirred for 6 hours. After the termination of reaction, water was added to the reaction mixture. The mixture was extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under the reduced pressure. The residue was purified by the recrystallization from AcOEt-hexane mixture solvent to give the title compound (112 mg) having the following physical data.

Workup

  1. additionwas added to the reaction mixture
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed
  4. customdried over and
  5. concentrationconcentrated under the reduced pressure
  6. customThe residue was purified by the recrystallization from AcOEt-hexane mixture solvent

Sources & evidence

ORD record
ord-a677d512286b423994c01bc2cda270f2
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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