1,5-Dibromopentane → 6-(5-bromopentoxy)-4,4-dimethyl-4H-3,1-benzoxazin-2-one

HRID 463061Notes

Reaction equation

HRID 463061 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH3:13])([CH3:12])[C:6]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br>CS(C)=O>[Br:21][CH2:22][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][C:7]([CH3:12])([CH3:13])[C:6]=2[CH:14]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 132604826-hydroxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 132604896-(5-bromopentoxy)-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 19.3 gm (0.1 mol) of 6-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one in 200 ml of dimethyl sulfoxide is mixed at ambient temperature with 41.5 gm (0.3 mol) of potassium carbonate and 92 gm (0.4 mol) of 1,5-dibromopentane, whereupon the temperature rises to 45° C. After stirring a further two hours, ice water is added, and the resulting mixture is extracted with chloroform. The chloroform phase is washed with water and dried with sodium sulfate, and the chloroform is distilled off. The residue is recrystallized from ethyl acetate/petroleum ether.

Workup

  1. customrises to 45° C
  2. extractionthe resulting mixture is extracted with chloroform
  3. washThe chloroform phase is washed with water
  4. dry with materialdried with sodium sulfate
  5. distillationthe chloroform is distilled off
  6. customThe residue is recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-94624531fa3a40dbbf91beb17f72f0b4
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

Loading…