Acetic Acid → HCID 13653299, compound

HRID 1638827Notes

Reaction equation

HRID 1638827 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]#[CH:13])[C:6]=2[CH:14]=1.[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2[CH2:21][CH2:22][CH2:23][CH2:24][C:16]1=2.C(O)(=O)C>O>[CH2:11]([N:7]1[C:6]2[CH:14]=[C:2]([N:1]3[C:18](=[O:19])[C:17]4[CH2:21][CH2:22][CH2:23][CH2:24][C:16]=4[C:15]3=[O:20])[CH:3]=[CH:4][C:5]=2[O:9][C:8]1=[O:10])[C:12]#[CH:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 13653298103361-38-2

Product 1

HCID 13653299HCID 13653299, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-amino-3-(2-propynyl)-3H-benzoxazol-2-one (0.50 g), 3,4,5,6-tetrahydrophthalic anhydride (0.53 g) and acetic acid (5 ml) was heated at 100° to 110° C. under reflux for 3 hours. After being allowed to cool, water was added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with water, neutralized with sodium bicarbonate solution, dried and concentrated to give 2-[3-(2-propynyl)-3H-benzoxazol-2-on-5-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.30 g). m.p., 285.5° C.

Workup

  1. temperaturewas heated at 100° to 110° C.
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-90255218ee874bad8444ffb705a02828
Source dataset
uspto-grants-1989_11
Patent number
US04880925

Reaction notes

Loading…