1,2-Dibromoethane → 6-(2-Bromoethoxy)-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

HRID 615214

Reaction equation

HRID 615214 reaction equation
[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:4]=2[O:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:21][CH2:22][CH2:23]Br>>[Br:21][CH2:22][CH2:23][O:13][C:10]1[CH:11]=[CH:12][C:4]2[O:3][C:2]([CH3:14])([CH3:1])[NH:7][C:6](=[O:8])[C:5]=2[CH:9]=1

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 137543316-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one

Product 1

HCID 137544136-(2-Bromoethoxy)-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

Procedure

A mixture of 48.2 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one, 70 g of potassium carbonate and 250 ml of 1,2-dibromoethane is refluxed for 4 hours whilst stirring. The semi-liquid reaction mixture is extracted 3 to 4 times whilst hot with 1 liter of methanol each time; the combined methanol extracts are concentrated by evaporation and the residue is recrystallised from methanol. 6-(2-Bromoethoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one having a melting point of 190°-195° is obtained.

Workup

  1. temperatureis refluxed for 4 hours
  2. customThe semi-liquid reaction mixture
  3. extractionis extracted 3 to 4 times whilst hot with 1 liter of methanol each time
  4. concentrationthe combined methanol extracts are concentrated by evaporation
  5. customthe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-02912c6359c547e6989e44c698526db1
Source dataset
uspto-grants-1985_02
Patent number
US04497813

Linked notes

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