2-(Oxiran-2-ylmethoxy)benzonitrile → 1-[2-(3-Carbamoyl-4-hydroxyphenoxy)-1,1-dimethylethylamino]-3-(2-cyanophenoxy)propan-2-ol

HRID 980271Notes

Reaction equation

HRID 980271 reaction equation
[NH2:1][C:2]([CH3:16])([CH3:15])[CH2:3][O:4][C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1.[O:17]1[CH2:29][CH:18]1[CH2:19][O:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>O1CCOCC1>[C:10]([C:9]1[CH:13]=[C:5]([CH:6]=[CH:7][C:8]=1[OH:14])[O:4][CH2:3][C:2]([NH:1][CH2:29][CH:18]([OH:17])[CH2:19][O:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24])([CH3:16])[CH3:15])(=[O:11])[NH2:12]

Participants

4

Reactant 2

HCID 126196712-(Oxiran-2-ylmethoxy)benzonitrileHCID 137544255-(2-Amino-2-methylpropoxy)salicylamide

Product 1

HCID 137543821-[2-(3-Carbamoyl-4-hydroxyphenoxy)-1,1-dimethylethylamino]-3-(2-cyanophenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The solution of 2.24 g of 5-(2-amino-2-methylpropoxy)salicylamide in 30 ml of dioxan is refluxed for 7 hours after the addition of 2.3 g of 2-(2,3-epoxypropoxy)benzonitrile, and then concentrated by evaporation. The residue is divided between 10 ml of 2N hydrochloric acid and 100 ml of ethyl acetate. The acidic aqueous phase is rendered alkaline with concentrated ammonia solution, the base is extracted with ethyl acetate and the solvent is evaporated off, whereupon an oil is obtained from which, by crystallisation from isopropanol and recrystallisation from ethyl acetate, 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-1,1-dimethylethylamino]-3-(2-cyanophenoxy)propan-2-ol having a melting point of 125°-126° is obtained.

Workup

  1. concentrationconcentrated by evaporation
  2. extractionthe base is extracted with ethyl acetate
  3. customthe solvent is evaporated off, whereupon an oil

Sources & evidence

ORD record
ord-97b0d4887591409db149f078b56f3609
Source dataset
uspto-grants-1987_01
Patent number
US04636511

Reaction notes

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