Phenyl-2-aminoethyl sulfide → N-cyano-N'-(2-phenylthioethyl)-4-pyridinecarboximidamide

HRID 327126Notes

Reaction equation

HRID 327126 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)OC(C)C)#[N:2].[C:15]1([S:21][CH2:22][CH2:23][NH2:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)=[N:24][CH2:23][CH2:22][S:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[N:2]

Participants

4

Reactant 2

HCID 37013Phenyl-2-aminoethyl sulfideHCID 10012715Isopropyl N-cyano-4-pyridinecarboximidate

Product 1

HCID 19734568N-cyano-N'-(2-phenylthioethyl)-4-pyridinecarboximidamideYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-4-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (5 ml), and 2-phenylthioethylamine (0.49 g, 3.2 mmol) was added. The mixture was stirred at room temperature for 2 hours After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 10 g) eluting with chloroform-methanol (50:1). The eluted fractions were concentrated under reduced pressure and crystallized from diethyl ether to give the title compound (0.49 g, 1.7 mmol, yield: 66%) as colorless crystals.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. concentrationthe residual concentrate
  3. washeluting with chloroform-methanol (50:1)
  4. concentrationThe eluted fractions were concentrated under reduced pressure
  5. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-358eb9e37feb4c008aeed5bfc85eaaf2
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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