3-Chloroaniline → HCID 178527342, compound

HRID 561043Notes

Reaction equation

HRID 561043 reaction equation
CO[C:3](=O)[C:4]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])=[CH:5][O:6]CC.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24]>C1(OC2C=CC=CC=2)C=CC=CC=1>[Cl:20][C:21]1[CH:22]=[C:23]2[C:25]([C:5]([OH:6])=[C:4]([S:9]([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)(=[O:10])=[O:11])[CH:3]=[N:24]2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 670001572-(4-Chloro-benzenesulfonyl)-3-ethoxy-acrylic acid methyl ester

Product 1

HCID 178527342HCID 178527342, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

The mixture of 2-(4-chloro-benzenesulfonyl)-3-ethoxy-acrylic acid methyl ester (7.62 g, 25 mmol) and 3-chloroaniline (3.19 g, 25 mmol) in diphenyl ether (20 ml) was heated at near reflux for 1 h. After cooling the precipitate was filtered and washed with ether to obtain 4.25 g of the title compound in 48.0% yield.

Workup

  1. temperaturewas heated
  2. temperatureat near reflux for 1 h
  3. temperatureAfter cooling the precipitate
  4. filtrationwas filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-4ca2f9bd631840ac962cd3378c56a323
Source dataset
uspto-grants-2011_11
Patent number
US08063220B2

Reaction notes

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