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

HRID 236263Notes

Reaction equation

HRID 236263 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-264aaf453ca64d8d8a08f0a5f36819bd
Source dataset
uspto-grants-1987_02
Patent number
US04643849

Reaction notes

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