4-Isopropylaniline → 2-Cyano-3-((4-isopropylphenyl)amino)-3-(methylthio)acrylamide

HRID 527262

Reaction equation

HRID 527262 reaction equation
[C:1]([C:3](=[C:7]([S:10][CH3:11])SC)[C:4]([NH2:6])=[O:5])#[N:2].[CH:12]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([CH3:14])[CH3:13]>C(O)C>[C:1]([C:3](=[C:7]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([CH:12]([CH3:14])[CH3:13])=[CH:16][CH:17]=1)[S:10][CH3:11])[C:4]([NH2:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 74644-IsopropylanilineHCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 867018702-Cyano-3-((4-isopropylphenyl)amino)-3-(methylthio)acrylamideYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1.50 g (2-cyano-3,3-bis(methylthio)acrylamide) in 15 mL of ethanol. was added 1.084 mL (1.0 eq.) of 4-isopropylaniline, 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-isopropylphenyl)amino)-3-(methylthio)acrylamide as an off white to light yellow powder as product. Product was allowed to dry under vacuum for 1 hr (1.360 g, 62% yield).

Workup

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

Sources & evidence

ORD record
ord-cd596e0608df4a178febd74bed6b17c7
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Linked notes

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