3-Chloroaniline → 3-((3-Chlorophenyl)amino)-2-cyano-3-(methylthio)acrylamide

HRID 2202607Notes

Reaction equation

HRID 2202607 reaction equation
[C:1]([C:3](=[C:7]([S:10][CH3:11])SC)[C:4]([NH2:6])=[O:5])#[N:2].[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16]>CCO>[Cl:12][C:13]1[CH:14]=[C:15]([NH:16][C:7]([S:10][CH3:11])=[C:3]([C:1]#[N:2])[C:4]([NH2:6])=[O:5])[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 866989553-((3-Chlorophenyl)amino)-2-cyano-3-(methylthio)acrylamideYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-cyano-3,3-bis(methylthio)acrylamide I-2 (5.0 g, 59.47 mmol) and 3-chloroaniline (8.346 g, 65.42 mmol) in EtOH (25 mL) was refluxed overnight. The reaction mixture was then allowed to cool to room temperature. The resulting solid was filtered and dried to give compound 3 (6.75 g, 45% yield, 100% purity) as a white solid.

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-0818ae36b3cd4186b2a87b34f182a1e6
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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