HCID 20506962, compound → HCID 13134778, compound

HRID 355106Notes

Reaction equation

HRID 355106 reaction equation
[C:1]([CH2:4][C:5]1[CH:21]=[CH:20][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([OH:19])=O)=[CH:7][CH:6]=1)(=[O:3])[NH2:2]>O>[O:19]=[C:17]1[CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]2[CH:20]=[CH:21][C:5]([CH2:4][C:1]([NH2:2])=[O:3])=[CH:6][C:7]1=2

Participants

3

Reactant 1

HCID 20506962HCID 20506962, compound

Product 1

HCID 13134778HCID 13134778, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 59 mg of 2-(4-carbamoylmethylphenoxy)phenylacetic acid was added 1.8 g of polyphosphoric acid, and the mixture was stirred under a dry atmosphere at 100° C. for 50 minutes. After being cooled, the resulting mixture was dissolved in water and then extracted with ethyl acetate. The extract was washed with a 1% sodium hydroxide solution and then with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a residue, which was recrystallized from acetone/n-hexane to give 45 mg (yield: 76%) of (10,11-dihydro-11-oxo dibenzo[b,f]oxepin-2-yl)-acetamide as light yellow crystals having a melting point of 151.5°-154° C.

Workup

  1. temperatureAfter being cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a 1% sodium hydroxide solution
  4. dry with materialwith a saturated sodium chloride solution and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customto obtain a residue, which
  7. customwas recrystallized from acetone/n-hexane

Sources & evidence

ORD record
ord-e148ce082e744760bb79657be9ebeec1
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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