1-Bromo-3-chloropropane → 7-(3-bromopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one

HRID 1462362Notes

Reaction equation

HRID 1462362 reaction equation
[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([OH:13])=[CH:12][C:4]=2[O:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:21][CH2:22][CH2:23][CH2:24]Cl>CC(C)=O>[Br:21][CH2:22][CH2:23][CH2:24][O:13][C:11]1[CH:10]=[CH:9][C:5]2[C:6](=[O:8])[NH:7][C:2]([CH3:14])([CH3:1])[O:3][C:4]=2[CH:12]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 137544122,3-dihydro-2,2-dimethyl-7-hydroxy-4H-1,3-benzoxazin-4-one

Product 1

HCID 204526527-(3-bromopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 38.6 g of 2,3-dihydro-2,2-dimethyl-7-hydroxy-4H-1,3-benzoxazin-4-one, 55.2 g of potassium carbonate, 47.2 g of 1-bromo-3-chloro-propane and 600 ml of acetone is refluxed for 24 hours. Filtering, concentrating the filtrate to 1/3 of the original volume and cooling yields 7-(3-bromopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one with a melting point of 111°-113°.

Workup

  1. temperatureis refluxed for 24 hours
  2. filtrationFiltering
  3. concentrationconcentrating the filtrate to 1/3 of the original volume
  4. temperaturecooling

Sources & evidence

ORD record
ord-da7746d3861248438b23e52c01b4d776
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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