4-Nitroaniline → 2-Cyano-3-(methylthio)-3-((4-nitrophenyl)amino)acrylamide

HRID 527257Notes

Reaction equation

HRID 527257 reaction equation
[C:1]([C:3](=[C:7]([S:10][CH3:11])SC)[C:4]([NH2:6])=[O:5])#[N:2].[N+:12]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([O-:14])=[O:13]>C(O)C>[C:1]([C:3](=[C:7]([S:10][CH3:11])[NH:19][C:18]1[CH:20]=[CH:21][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)[C:4]([NH2:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 867018672-Cyano-3-(methylthio)-3-((4-nitrophenyl)amino)acrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolved 10.00 g 2-cyano-3,3-bis(methylthio)acrylamide in 100 mL of ethanol. Then added 7.337 g (1.00 eq.) of 4-nitroaniline 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 2-cyano-3-(methylthio)-3-((4-nitrophenyl)amino)acrylamide as an off white to light yellow powder as product. The product was allowed to dry under vacuum for 1 hr.

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-ed8535276b4b4e4a89dfb4e799999d01
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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