Norfenefrine → HCID 178512328, compound

HRID 236262Notes

Reaction equation

HRID 236262 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[N:13]=[C:14]([NH:17][C:18]([NH2:20])=[NH:19])[S:15][CH:16]=1)SC)#[N:2].[CH:21]1[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([CH:28]([OH:31])[CH2:29][NH2:30])[CH:22]=1>[N+]([O-])([O-])=O.[Ag+].C(O)C>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[N:13]=[C:14]([NH:17][C:18]([NH2:20])=[NH:19])[S:15][CH:16]=1)=[N:30][CH2:29][CH:28]([OH:31])[C:23]1[CH:22]=[CH:21][CH:26]=[C:25]([OH:27])[CH:24]=1)#[N:2]

Participants

5

Reactant 2

HCID 4538NorfenefrineHCID 178503873HCID 178503873, compound

Product 1

HCID 178512328HCID 178512328, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

With 15 ml of ethanol were mixed 3.0 g of N-cyano-N'-{2-[(2-guanidino-4-thiazolyl)methylthio]ethyl}-S-methylisothiourea, 4.9 g of DL-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]amine and 1.97 g of silver nitrate, and the resulting mixture was subjected to reaction under reflux for 1.5 hours. After completion of the reaction, the insolubles were removed by filtration, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:methanol=5:1 by volume) and crystallized from methanol to obtain 2.5 g (yield 68%) of N-cyano-N'-{2-[(2-guanidino-4-thiazolyl)methylthio]ethyl}-N"-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]guanidine having a melting point of 162°-164° C.

Workup

  1. customthe resulting mixture was subjected to reaction
  2. temperatureunder reflux for 1.5 hours
  3. customAfter completion of the reaction
  4. customthe insolubles were removed by filtration
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe resulting residue was purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:methanol=5:1 by volume)
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-859bc73aced9499faaab618719f41849
Source dataset
uspto-grants-1987_02
Patent number
US04643849

Reaction notes

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