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

HRID 1784916Notes

Reaction equation

HRID 1784916 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:17](#[N:21])[CH2:18][C:19]#[N:20].[C:22]1([SH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C(O)C>[NH2:20][C:19]1[C:18]([C:17]#[N:21])=[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:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:2]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8010MalononitrileHCID 8471TriethylamineHCID 33296N-(4-(2,2-Dicyanoethenyl)phenyl)acetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

19 g (0.09 mol) of N-[4-(2,2-dicyanovinyl)phenyl]acetamide, 5.95 g (0.09 mol) of malononitrile and 9.91 g (0.09 mol) of thiophenol are initially charged in 120 ml of ethanol, and 0.4 ml of triethylamine are added. The mixture is stirred at reflux for 2 h, during which the product crystallizes. After cooling, the product is filtered off with suction and dried under reduced pressure.

Workup

  1. temperatureat reflux for 2 h, during which the product
  2. customcrystallizes
  3. temperatureAfter cooling
  4. filtrationthe product is filtered off with suction
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c08b117f2676448eb81e4c74ab745903
Source dataset
uspto-grants-2009_03
Patent number
US07504421B2

Reaction notes

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