Acetic Acid → N-(3-chloropropyl)-6-acetyl-2-benzoxazolinone

HRID 744510Notes

Reaction equation

HRID 744510 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14].[C:15](O)(=[O:17])[CH3:16]>>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[CH:13][C:8]=2[O:7][C:6]1=[O:14]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 100360722(3H)-Benzoxazolone, 3-(3-chloropropyl)-

Product 1

HCID 10400030N-(3-chloropropyl)-6-acetyl-2-benzoxazolinone

Conditions

Temperature
100 °C

Procedure

A mixture of N-(3-chloropropyl)-2-benzoxazolinone (8.5 g, 40 mmol), polyphosphoric acid (100 g), and acetic acid (2.4 g, 2.3 ml, 40 mmol), was stirred and heated at 100° C. for 2 hours. The hot solution was poured into ice-water to deposit a yellow gum. The mixture was extracted with dichloromethane, and insolubles were filtered. The dichloromethane extract was washed with water, dried (K2O3), and concentrated to afford 6.4 g of a slightly green solid. This was recrystallized from ethanol (95%) to yield N-(3-chloropropyl)-6-acetyl-2-benzoxazolinone as a brown solid, 3.5 g, m.p.=100°-103° C.

Workup

  1. extractionThe mixture was extracted with dichloromethane, and insolubles
  2. filtrationwere filtered
  3. extractionThe dichloromethane extract
  4. washwas washed with water
  5. customdried (K2O3)
  6. concentrationconcentrated
  7. customto afford 6.4 g of a slightly green solid
  8. customThis was recrystallized from ethanol (95%)

Sources & evidence

ORD record
ord-f9c452462f19436b85bf9c83626ad20b
Source dataset
uspto-grants-1996_09
Patent number
US05559126

Reaction notes

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