Acetic Acid → HCID 13653299, compound

HRID 235578Notes

Reaction equation

HRID 235578 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, neuralized 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, neuralized with sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-04b58a94b0df46b5b0a83787543df744
Source dataset
uspto-grants-1987_02
Patent number
US04640707

Reaction notes

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