Potassium Carbonate → 4-[(2-Oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)oxy]butyl acetate

HRID 463062Notes

Reaction equation

HRID 463062 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][CH2:7][C:6]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)(=[O:21])[CH3:20]>CS(C)=O>[C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][CH2:7][C:6]=2[CH:12]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 132604846-hydroxy-2,4-dihydro-1H-3,1-benzoxazin-2-one

Product 1

HCID 132604944-[(2-Oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)oxy]butyl acetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

One hundred two grams (0.62 mol) of 6-hydroxy-4H-3,1-benzoxazin-2-one are dissolved in 1 liter of dimethylsulfoxide and mixed with 227 gm (1.64 mol) of potassium carbonate and 166 gm (0.73 mol) of 4-acetoxy-butylbromide. The reaction mixture is stirred for six hours at 50° C., and then ice water is added. The precipitate is subjected to suction filtration, washed with water, and dried.

Workup

  1. filtrationThe precipitate is subjected to suction filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-887f993626cf4a8e9077eccda071cc62
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

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