Phenylethanolamine → N-cyano-N'-(beta-hydroxyphenethyl)-N"-{2-[(5-methyl-4-imidazolyl)methylthio]ethyl}guanidine

HRID 1650206Notes

Reaction equation

HRID 1650206 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[N:13]=[CH:14][NH:15][C:16]=1[CH3:17])SC)#[N:2].[CH:18]1[CH:23]=[CH:22][C:21]([CH:24]([OH:27])[CH2:25][NH2:26])=[CH:20][CH:19]=1>C(O)C>[C:1]([NH:3][C:4]([NH:26][CH2:25][CH:24]([OH:27])[C:21]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1)=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[N:13]=[CH:14][NH:15][C:16]=1[CH3:17])#[N:2]

Participants

4

Reactant 2

HCID 1000PhenylethanolamineHCID 1036301-Cyano-2-methyl-3-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)isothiourea

Product 1

HCID 178433681N-cyano-N'-(beta-hydroxyphenethyl)-N"-{2-[(5-methyl-4-imidazolyl)methylthio]ethyl}guanidineYield 20.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With 5 ml of ethanol were mixed 1 g of N-cyano-N'-{2-[(5-methyl-4-imidazolyl)methylthio]ethyl}-S-methylisothiourea and 2.6 g of DL-β-hydroxyphenethylamine, and the resulting mixture was subjected to reaction under reflux for 5 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the oily substance thus obtained was washed with 20 ml of diethyl ether and then purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:methanol=10:1 by volume) to obtain 0.27 g (yield 20%) of amorphous N-cyano-N'-(β-hydroxyphenethyl)-N"-{2-[(5-methyl-4-imidazolyl)methylthio]ethyl}guanidine.

Workup

  1. customthe resulting mixture was subjected to reaction
  2. temperatureunder reflux for 5 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe oily substance thus obtained
  6. washwas washed with 20 ml of diethyl ether
  7. custompurified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:methanol=10:1 by volume)

Sources & evidence

ORD record
ord-b73d1b33fded4be58b816341eed9ba86
Source dataset
uspto-grants-1990_05
Patent number
US04923882

Reaction notes

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