N,N-dimethyl-p-phenylenediamine → 2-Cyano-3-((4-(dimethylamino)phenyl)amino)-3-(methylthio)acrylamide

HRID 527254

Reaction equation

HRID 527254 reaction equation
[C:1]([C:3](=[C:7]([S:10][CH3:11])SC)[C:4]([NH2:6])=[O:5])#[N:2].[CH3:12][N:13]([CH3:21])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1>C(O)C>[C:1]([C:3](=[C:7]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]([CH3:21])[CH3:12])=[CH:15][CH:16]=1)[S:10][CH3:11])[C:4]([NH2:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 867018642-Cyano-3-((4-(dimethylamino)phenyl)amino)-3-(methylthio)acrylamideYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1.00 g (2-cyano-3,3-bis(methylthio)acrylamide) in 25 mL of ethanol was added 0.720 g (1.1 eq.) of N,N-dimethyl-p-phenylenediamine and the reaction was stirred at 75° C. until starting amide was absent as confirmed by HPLC. Once complete (18 hrs), the reaction was brought to room temperature and filtered to obtain 2-cyano-3-((4-(dimethylamino)phenyl)amino)-3-(methylthio)acrylamide as an off white to light yellow powder. The product was allowed to dry under vacuum for 1 hr (1.133 g, 91% yield).

Workup

  1. customOnce complete (18 hrs)
  2. customwas brought to room temperature
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b2608096b06a4003b60feb0cb28595c8
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Linked notes

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