Water → 2(3H)-Benzoxazolone, 3-(3-chloropropyl)-

HRID 2211517Notes

Reaction equation

HRID 2211517 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]1=[O:12].[Cl:13][CH2:14][CH2:15][CH2:16]Br.O>CN(C)C=O>[Cl:13][CH2:14][CH2:15][CH2:16][N:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:3][C:4]1=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 60432(3H)-BenzoxazoloneHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydride

Product 1

HCID 100360722(3H)-Benzoxazolone, 3-(3-chloropropyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of sodium hydride (7.8 g, 0.16 mol, ether-washed) in dimethylformamide (75 ml) was added dropwise under nitrogen, 2-benzoxazolinone (20.0 g, 0.15 mol) dissolved in dimethylformamide (150 ml). After complete addition the reaction was stirred at ambient temperature for 30 min. and then it was cooled to −5° C. with an ice-acetone bath. A solution of 3-chloro-1-bromopropane (46.6 g, 0.30 mol) in dimethylformamide (50 ml) was added dropwise (temperature never exceeded 0° C.). The reaction was allowed to reach ambient temperature and was stirred for 16 hours. The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed with water, dried (MgSO4), and the extract concentrated from toluene-hexane to afford N-(3-chloropropyl)-2-benzoxazolinone as large needles, 15.6 g, m.p.=264°-266° C.

Workup

  1. additionwas added dropwise under nitrogen
  2. additionAfter complete addition the reaction
  3. temperatureit was cooled to −5° C. with an ice-acetone bath
  4. customto reach ambient temperature
  5. stirringwas stirred for 16 hours
  6. extractionthe aqueous mixture was extracted with ethyl acetate
  7. washThe ethyl acetate was washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationthe extract concentrated from toluene-hexane

Sources & evidence

ORD record
ord-795037d93e7641ef88a9facb48490fc8
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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