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

HRID 1955880Notes

Reaction equation

HRID 1955880 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

N-(3chloropropyl)-6-aetyl-2-benzoxazolinone 7 8 A mixture of N-(3-chloropropyl)-2-benzoxazolinone (8.5 g, 40 mmol), 9 polyphosphoric acid (100 g), and acetic acid (2.4 g, 2.3 ml, 40 mmol), was stirred and 10 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 11 filtered. The dichloromethane extract was washed with water, dried (K2CO), and 12 concentrated to afford 6.4 g of a slightly green solid. This was recrystallized from 13 ethanol (95%) to yield N-(3-chloropropyl}6acetyl-2-benzoxazolinone as a brown solid, 14 3.5 g, m.p.=100°-103° C. 15

Workup

  1. extractionThe mixture was extracted with dichloromethane, and insolubles
  2. filtrationfiltered
  3. extractionThe dichloromethane extract
  4. washwas washed with water
  5. customdried (K2CO), and 12
  6. concentrationconcentrated
  7. customto afford 6.4 g of a slightly green solid
  8. customThis was recrystallized from 13 ethanol (95%)

Sources & evidence

ORD record
ord-063e1d1a4a184e27b1eefc2604097802
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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