1-(Oxiran-2-yl)ethan-1-ol → 1-[4-(3-Chlorobenzyloxy)phenylamino] butane-2,3-diol

HRID 330495Notes

Reaction equation

HRID 330495 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.[O:17]1[CH:19]([CH:20]([OH:22])[CH3:21])[CH2:18]1>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][CH2:21][CH:20]([OH:22])[CH:19]([OH:17])[CH3:18])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 115934311-(Oxiran-2-yl)ethan-1-olHCID 141824334-[(3-Chlorophenyl)methoxy]aniline

Product 1

HCID 141824341-[4-(3-Chlorobenzyloxy)phenylamino] butane-2,3-diolYield 50.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution containing 50 g (0.21 mol) of 4-(3'-chlorobenzyloxy) aniline and 21.6 g (0.24 mol) of the mixture obtained in Example 1 in 850 ml of isopropanol is refluxed for 6 hrs 30 mins. When the isopropanol has evaporated, the crude mixture is purified by flash silica chromatography (eluant: CH2Cl2 --CH3OH: 97-3). 34 g (yield: 49%) of white solid is recovered, corresponding to the product expected and having a melting point of from 95°-96° C.

Workup

  1. temperatureis refluxed for 6 hrs 30 mins
  2. customWhen the isopropanol has evaporated
  3. customthe crude mixture is purified by flash silica chromatography (eluant: CH2Cl2 --CH3OH: 97-3)

Sources & evidence

ORD record
ord-ac81e5ab09be41849730441ef2b47868
Source dataset
uspto-grants-1990_01
Patent number
US04897409

Reaction notes

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