Pyridine → Methyl 4-{[4-(methanesulfonyl)benzene-1-sulfonyl]amino}benzoate

HRID 1676955Notes

Reaction equation

HRID 1676955 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.N1C=CC=CC=1.[CH3:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:28]([C:25]2[CH:24]=[CH:23][C:22]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:27][CH:26]=2)(=[O:30])=[O:29])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 12082Methyl 4-aminobenzoateHCID 27351824-Methanesulfonylbenzene-1-sulfonyl chloride

Product 1

HCID 46534828Methyl 4-{[4-(methanesulfonyl)benzene-1-sulfonyl]amino}benzoateYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 4-amino-benzoic acid methyl ester (0.594 g, 3.93 mmol) in a mixture of dichloromethane (15 mL)/pyridine (15 mL) is added 4-methanesulfonyl benzenesulfonyl chloride (1.0 g, 3.93 mmol) and the mixture is allowed to react for 6 h at ambient temperature. The reaction is diluted with ethyl acetate and washed with 1N HCl. The organic layer is separated and dried over sodium sulfate, filtered, and concentrated to give 1.26 g (87%) of the title compound. MS (ES−) (m/e) 368.0 (M−1)−.

Workup

  1. customto react for 6 h at ambient temperature
  2. washwashed with 1N HCl
  3. customThe organic layer is separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e59db2d346b4892b5a562de121dd395
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

Loading…