Phenethylamine → HCID 178433302, compound

HRID 866420Notes

Reaction equation

HRID 866420 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])SC)#[N:2].[C:18]1([CH2:24][CH2:25][NH2:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])=[N:26][CH2:25][CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)#[N:2]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 178503877HCID 178503877, compound

Product 1

HCID 178433302HCID 178433302, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-S-methylisothiourea (2.69 g) and 2-phenylethylamine (7.2 g) in acetonitrile (50 ml) was heated under reflux for 24 hours. Following concentration and ether extraction to remove excess 2-phenylethylamine the crude product was chromatographed on a column of silica gel and eluted with ethyl acetate-isopropyl alcohol (4:1). Recrystallisation from ethanol-ether afforded the title compound (1.4 g) m.p. 135°-136°. (Found: C, 59.8; H, 6.8; N, 24.8; S, 9.4% C17H22N6S requires: C, 59.6; H, 6.5; N, 24.5; S, 9.4%).

Workup

  1. temperatureunder reflux for 24 hours
  2. concentrationconcentration and ether extraction
  3. customto remove excess 2-phenylethylamine the crude product
  4. customwas chromatographed on a column of silica gel
  5. washeluted with ethyl acetate-isopropyl alcohol (4:1)
  6. customRecrystallisation from ethanol-ether

Sources & evidence

ORD record
ord-38acf1576b394255821da8558d843330
Source dataset
uspto-grants-1978_07
Patent number
US04098898

Reaction notes

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