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

HRID 1856554Notes

Reaction equation

HRID 1856554 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.[OH-].[Na+].O.Br[CH2:16][CH2:17][CH2:18][Cl:19]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.CC1C=CC=CC=1>[Cl:19][CH2:18][CH2:17][CH2:16][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][C:3]1=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 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 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred mixture of 9 parts of 2H-1,4-benzoxazin-3(4H)-one, 0.9 parts of N,N,N-triethylbenzenemethanaminium chloride, 9 parts of sodium hydroxide solution 50% and 24 parts of water are added 10.4 parts of 1-bromo-3-chloropropane at 30° C. The whole is heated to 90° C. and stirring is continued for 3 hours at this temperature. The reaction mixture is cooled to about 70° C., methylbenzene is added and the whole is stirred overnight at room temperature. The organic phase is separated, dried, filtered and evaporated, yielding 10 parts of 4-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-one as a residue.

Workup

  1. temperatureThe reaction mixture is cooled to about 70° C.
  2. stirringthe whole is stirred overnight at room temperature
  3. customThe organic phase is separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3a21dc9e6b4c4840b8fc16f22fb415c1
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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