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

HRID 55618

Reaktionsgleichung

Reaktionsgleichung von HRID 55618
[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]

Komponenten

3

Edukt 2

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

Produkt 1

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

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-164805ce9e984166850d66a6ca37494f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624927

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