Ethanol → 4-S-Cysteaminylphenol

HRID 565132Notes

Reaction equation

HRID 565132 reaction equation
C(O)C.[SH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Cl.Br[CH2:14][CH2:15][NH2:16].C(=O)([O-])[O-].[K+].[K+]>O>[NH2:16][CH2:15][CH2:14][S:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 122086202-BROMOETHYLAMINE HYDROCHLORIDE

Product 1

HCID 1153474-S-CysteaminylphenolYield 105.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of ethanol, 1.2 g of 4-mercaptophenol, 2.1 g of 2-bromoethylamine hydrochloride and 1.4 g of potassium carbonate were added, followed by stirring for 3 hours at room temperature. Water was added, and the resulting mixture was extracted with ethyl ether. The extract was dried over MgSO4 and the ethyl ether was distilled off under reduced pressure, whereby 1.7 g of the compound (7) were obtained (yield: stoichiometric).

Workup

  1. extractionthe resulting mixture was extracted with ethyl ether
  2. dry with materialThe extract was dried over MgSO4
  3. distillationthe ethyl ether was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2646573ad4b6454fa3ec5fafbd90e11c
Source dataset
uspto-grants-2001_01
Patent number
US06171520B2

Reaction notes

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