Ethanol → N-{4-[2-Amino-3,5-dicyano-6-(phenylsulphanyl)-4-pyridinyl]phenyl}acetamide

HRID 1825299Notes

Reaction equation

HRID 1825299 reaction equation
[C:1]([C:3]([C:15]#[N:16])=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)#[N:2].C(#N)[CH:18]([CH2:20][C:21]#[N:22])O.[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)C.C([N:36](CC)CC)C>>[NH2:22][C:21]1[C:20]([C:18]#[N:36])=[C:4]([C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=2)[C:3]([C:15]#[N:16])=[C:1]([S:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:2]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 7969ThiophenolHCID 8471TriethylamineHCID 33296N-(4-(2,2-Dicyanoethenyl)phenyl)acetamideHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 12016387N-{4-[2-Amino-3,5-dicyano-6-(phenylsulphanyl)-4-pyridinyl]phenyl}acetamide

Procedure

318 g (1.5 mol) of N-[4-(2,2-dicyanovinyl)phenyl]acetamide, 99 g (1.5 mol) of malonitrile and 166 g (1.5 mol) of thiophenol are initially introduced in 2 000 ml of ethanol, and 6.7 ml of triethylamine are then added. The mixture is stirred under reflux for 2 hours, in connection with which crystallization takes place. After the mixture has cooled down to room temperature, the product is filtered off with suction and dried in vacuo.

Workup

  1. additionare then added
  2. temperatureunder reflux for 2 hours, in connection with which crystallization
  3. filtrationthe product is filtered off with suction
  4. customdried in vacuo

Sources & evidence

ORD record
ord-475cce6f5d1c4c04b1b150097e163411
Source dataset
uspto-grants-2006_05
Patent number
US07045631B2

Reaction notes

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