Isopropanol → 4-(3,4-Dichlorophenyl)-2-oxazolone

HRID 47937

Reaction equation

HRID 47937 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=O.[O-:13][C:14]#[N:15].[K+].CC(O)C>C(O)(=O)C>[Cl:12][C:7]1[CH:6]=[C:5]([C:3]2[NH:15][C:14](=[O:13])[O:1][CH:2]=2)[CH:10]=[CH:9][C:8]=1[Cl:11]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 70621931-(3,4-Dichlorophenyl)-2-hydroxyethan-1-oneHCID 11378442Potassium cyanate

Product 1

HCID 129929604-(3,4-Dichlorophenyl)-2-oxazoloneYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-hydroxy-3′,4′-dichloroacetophenone (10.3 g), potassium cyanate (8.1 g) and 2-propanol (100 mL) was heated to 50° C., and acetic acid (6.0 g) was slowly added dropwise. The mixture was stirred at 50° C. for 2 h. The reaction mixture was concentrated and poured into iced water (200 mL). The precipitated solid was collected by filtration, washed with water and air-dried to give the title compound as crystals (6.0 g, 52%). Recrystallization from tetrahydrofuran-hexane gave pale-yellow prism crystals. melting point: 262-263° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into iced water (200 mL)
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-f9b40148f4db4f7fb5c5398439a6374c
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Linked notes

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