Chlorosulfonic acid → 4-(2-((5-Chloro-2-methoxyphenyl)formamido)ethyl)benzene-1-sulfonyl chloride

HRID 2266402

Reaction equation

HRID 2266402 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:24][CH3:25])=[C:11]([CH:23]=1)[C:12]([NH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13]>ClCCl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:24][CH3:25])=[C:11]([CH:23]=1)[C:12]([NH:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:21][CH:22]=1)=[O:13]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1185755-chloro-2-methoxy-N-(2-phenylethyl)benzamide

Product 1

HCID 44545764-(2-((5-Chloro-2-methoxyphenyl)formamido)ethyl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.5 ml chlorosulfonic acid were added in one portion to 6.5 g 5-Chloro-2-methoxy-N-phenethyl-benzamide. The reaction mixture was stirred at room temperature for one hour, then 100 ml dichloromethane were added and the reaction mixture was poured on ice water. The organic layer was separated washed twice with 50 ml brine and then dried over MgSO4. The solvent was removed in vacuo to obtain 5.53 g 4-[2-(5-Chloro-2-methoxy-benzoylamino)-ethyl]-benzenesulfonyl chloride.

Workup

  1. additionthe reaction mixture was poured on ice water
  2. customThe organic layer was separated
  3. washwashed twice with 50 ml brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0c300a18388c493fb0bf603caca3c355
Source dataset
uspto-grants-2010_12
Patent number
US07858647B2

Linked notes

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