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

HRID 892793Notes

Reaction equation

HRID 892793 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-1b7db8f22bd240aba66e4bd745e78902
Source dataset
uspto-grants-1992_06
Patent number
US05120746

Reaction notes

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