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

HRID 374179Notes

Reaction equation

HRID 374179 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-pyridinecarboximidamide

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

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-bb1472f932f348a68f7dbe12a3bca3e5
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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