Ethanolamine → 2-[(2-Hydroxyethyl)amino]-4-phenyl-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile

HRID 885661Notes

Reaction equation

HRID 885661 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1.[OH:25][CH2:26][CH2:27][NH2:28].CO.O>CN(C)C=O>[OH:25][CH2:26][CH2:27][NH:28][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 887MethanolHCID 962WaterHCID 120183412-Chloro-4-phenyl-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile

Product 1

HCID 589687732-[(2-Hydroxyethyl)amino]-4-phenyl-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 0.7 g (2 mmol) of 2-chloro-4-phenyl-6-(phenylsulfanyl)-3,5-pyridine-dicarbonitrile (1st step) is dissolved in 2 ml of dimethylformamide (DMF), 0.27 g (4.5 mmol) of 2-hydroxyethylamine is added and the mixture is stirred at room temperature for 15 minutes. After addition of 2 ml of methanol, about 1 ml of water is added dropwise and the precipitate is filtered off with suction. The crystals are purified by boiling with 4 ml of methanol.

Workup

  1. additionis added dropwise
  2. filtrationthe precipitate is filtered off with suction
  3. customThe crystals are purified

Sources & evidence

ORD record
ord-caa5503ce00d4c608fda111c8e230834
Source dataset
uspto-grants-2012_08
Patent number
US08242281B2

Reaction notes

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