Methyl iodide → 2-(2-(3,4-Dichloro-N-methylphenylsulfonamido)phenyl)-acetic acid methyl ester

HRID 1642118Notes

Reaction equation

HRID 1642118 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)(=[O:14])=[O:13].CI.[C:26]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]([CH3:26])[S:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 667562102-(2-(3,4-Dichlorophenylsulfonamido)phenyl)acetic acid methyl ester

Product 1

HCID 667559532-(2-(3,4-Dichloro-N-methylphenylsulfonamido)phenyl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(2-(3,4-Dichlorophenylsulfonamido)phenyl)acetic acid methyl ester (14.3 g, 38.21 mmol) and methyl iodide (8.2 ml, 132.25 mmol) were dissolved in acetone (300 ml); K2CO3 (7.3 g, 52.90 mmol) was added thereto, and stirring was carried out overnight at 40° C. in a closed flask. The suspension was cooled and then filtered, concentrated, filtered over silica gel (eluant DCM) and concentrated.

Workup

  1. temperatureThe suspension was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. filtrationfiltered over silica gel (eluant DCM)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba65dc47405d4c89b22167fc74c985ff
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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