4-Isopropylaniline → 2-Cyano-3-((4-isopropylphenyl)amino)-3-(methylthio)acrylamide
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
Product 1
Reagents, catalysts & solvents 1
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
- customOnce complete (18 hrs)
- customwas brought to room temperature
- filtrationfiltered
Sources & evidence
- ORD record
- ord-b1d396204d4343fba54a99f2a3a2bdcf
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382237B2
Reaction notes
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