2-Mercaptoethanol → HCID 18319029, compound

HRID 1700933Notes

Reaction equation

HRID 1700933 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11]Br)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[SH:26][CH2:27][CH2:28][OH:29]>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11][S:26][CH2:27][CH2:28][OH:29])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 11291348HCID 11291348, compound

Product 1

HCID 18319029HCID 18319029, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[bis(4-chlorophenyl)methoxy]ethyl bromide (5.13 g, 14.2 mmol) in N,N-dimethylformamide (50 ml) was treated at 22° C. with powdered anhydrous potassium carbonate (3.0 g, 21.7 mmol) followed by 2-mercaptoethanol (1.25 g, 16.0 mmol). The resulting mixture was stirred at 22° for 18 h. The reaction mixture was then diluted with toluene (400 ml) washed with water, brine and dried over magnesium sulfate. Evaporation of the solvent gave an oil which was chromatographed on silica gel (elution ethyl acetate 0-10% in toluene) to give 4.93 g (96%) of the title material as a clear oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave an oil which
  5. customwas chromatographed on silica gel (elution ethyl acetate 0-10% in toluene)

Sources & evidence

ORD record
ord-656b582300d449e6955c04b1227b2fb0
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

Loading…