Pyridine → 2-(2-(3,4-Dichlorophenylsulfonamido)phenyl)acetic acid methyl ester

HRID 1642117Notes

Reaction equation

HRID 1642117 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11].N1C=CC=CC=1.[Cl:19][C:20]1[CH:21]=[C:22]([S:27](Cl)(=[O:29])=[O:28])[CH:23]=[CH:24][C:25]=1[Cl:26]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:27]([C:22]1[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([Cl:19])[CH:21]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 5743389Methyl 2-aminobenzeneacetate

Product 1

HCID 667562102-(2-(3,4-Dichlorophenylsulfonamido)phenyl)acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Aminophenylacetic acid methyl ester (10.2 g, 39.45 mmol) was dissolved in DCM (200 ml). There were then added first pyridine (12.4 ml, 151.71 mmol) and 3,4-dichlorobenzenesulfonyl chloride (11.8 ml, 75.87 mmol) in DCM (50 ml). The reaction solution was stirred overnight and then diluted with DCM and washed in succession with 0.5 M KHSO4 solution, saturated NaHCO3 solution and saturated NaCl solution, dried over sodium sulfate and concentrated. Purification was carried out by column chromatography on silica gel (DCM).

Workup

  1. washwashed in succession with 0.5 M KHSO4 solution, saturated NaHCO3 solution and saturated NaCl solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification

Sources & evidence

ORD record
ord-425520c5ca464d849f3d885d78a5a2a9
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

Loading…