Sulfuric Acid → HCID 12881958, compound

HRID 1577987Notes

Reaction equation

HRID 1577987 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[O:12][C:11]3[CH:14]=[CH:15][C:16]([C:18]([OH:20])=[O:19])=[CH:17][C:10]=3[NH:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH:26](O)([CH3:28])[CH3:27]>>[CH3:1][O:2][C:3]1[C:13]2[O:12][C:11]3[CH:14]=[CH:15][C:16]([C:18]([O:20][CH:26]([CH3:28])[CH3:27])=[O:19])=[CH:17][C:10]=3[NH:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 12881951HCID 12881951, compound

Product 1

HCID 12881958HCID 12881958, compoundYield 90%

Procedure

A mixture of 10,11-dihydro-4-methoxydibenz[b,f][1,4]oxazepine-8-carboxylic acid (3 g), isopropanol (30 ml) and concentrated sulfuric acid (0.5 ml) was refluxed for 10 hours and then the solvent used was distilled off. The residue was dissolved in ethyl acetate (50 ml) and, after washing with water, dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was recrystallized from ethanol to give isopropyl 10,11-dihydro-4-methoxydibenz[b,f][1,4]oxazepine-8-carboxylate as colorless needles. (Yield: 90%, m.p. 109.5°-110.5° C.)

Workup

  1. temperaturewas refluxed for 10 hours
  2. distillationthe solvent used was distilled off
  3. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  4. washafter washing with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-54b17f51dd6a4be184c78266b70e235d
Source dataset
uspto-grants-1981_09
Patent number
US04290953

Reaction notes

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