1-Bromo-3-chloropropane → 4-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 2362950Notes

Reaction equation

HRID 2362950 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22]>CN(C)C=O.C(OCC)(=O)C>[Cl:22][CH2:21][CH2:20][CH2:19][N:4]1[C:3](=[O:11])[CH2:2][O:1][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]1=2

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 727572H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 233451504-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2H-1,4-benzoxazin-3(4H)-one (1.0 g, 6.7 mmol) and potassium carbonate (1.4 g, 10.05 mmol) in N,N-dimethylformamide (20 mL), was added 1-bromo-3-chloropropane (1.99 mL, 20.1 mmol, d=1.6). After stirring at 60° C. for 60 hours, the reaction mixture was diluted with ethyl acetate (100 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgSO4 and concentrated to the title compound (1.46 g, 97%); 1H NMR (DMSO-d6): δ 1.99-2.03 (m, 2H), 3.71 (t, 2H, J=6.4 Hz), 4.00-4.04 (m, 2H), 4.63 (s, 2H), 7.00-7.01 (m, 2H), 7.03-7.09 (m, 1H), 7.22 (d, 1H, J=7.6 Hz); MS for C11H12ClNO2 m/z 225.96 (M+H)+.

Workup

  1. washwashed with dilute citric acid, water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated to the title compound (1.46 g, 97%)

Sources & evidence

ORD record
ord-d2189d83d4f24eacacff7e573b5de42e
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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