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

HRID 527273

Reaction equation

HRID 527273 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]>C(O)C>[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 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolved 7.00 g (2-cyano-3,3-bis(methylthio)acrylamide) in 125 mL of ethanol. Then added 4.348 mL (1.10 eq.) of 3-chloroaniline to the reaction vessel and stirred the reaction at 75° C. until starting amide was absent and confirmed by HPLC. Once complete (18 hrs), the reaction was brought to room temperature and filtered to obtain 3-((3-chlorophenyl)amino)-2-cyano-3-(methylthio)acrylamide as an off white to light yellow powder. Product was allowed to dry under vacuum for 1 hr (6.0 g, 57% yield).

Workup

  1. customthe reaction at 75° C.
  2. customOnce complete (18 hrs)
  3. customwas brought to room temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-13c5edb632ed4d19a0e351cf17c50515
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Linked notes

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