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

HRID 2184527Notes

Reaction equation

HRID 2184527 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 (K2CO3), 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. dry with materialdried (K2CO3)
  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-a01d10dea5fe42168e9d7c586b38cab2
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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