Acetic Anhydride → HCID 20337291, compound

HRID 1706139Notes

Reaction equation

HRID 1706139 reaction equation
C([N:4]1[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2[CH:17]=[C:18]([O:27]C(=O)C)[C:19]([O:23]C(=O)C)=[C:20]([S:21][CH3:22])[C:7]=2[CH2:6][CH2:5]1)(=O)C.C(OC(=O)C)(=[O:33])C.I([O-])(=O)(=O)=O.[Na+]>N1C=CC=CC=1.CO>[OH:23][C:19]1[C:18]([OH:27])=[CH:17][C:8]2[CH:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][NH:4][CH2:5][CH2:6][C:7]=2[C:20]=1[S:21]([CH3:22])=[O:33]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 20337279HCID 20337279, compoundHCID 23667635Sodium periodate

Product 1

HCID 20337291HCID 20337291, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

A solution of 8.6 g (20 mm) of 3-acetyl-7,8-diacetoxy-1-phenyl-6-methylthio-2,3,4,5-tetrahydro-1H-3-benzazepine (prepared by reacting the dihydroxy parent with an excess of acetic anhydride in pyridine at room temperature) in 40 ml of methanol at -5° is treated with 40 ml of 0.52 M sodium periodate (20.8 mm) dropwise over 15 minutes at 0°. The mixture is cooled overnight, then filtered to give a solid which is washed with methylene chloride. The organic extracts are combined, dried and evaporated in vacuo. The residue is heated at reflux in ethanolic hydrochloric acid overnight. The volatiles are removed and the residue taken up in water. Neutralization with ammonia and extraction with ethyl acetate gives the desired 7,8-dihydroxy-6-methylsulfinyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine. The hydrochloride salt is formed by treatment with ethereal hydrogen chloride.

Workup

  1. customat room temperature
  2. customat -5°
  3. temperatureThe mixture is cooled overnight
  4. filtrationfiltered
  5. customto give a solid which
  6. washis washed with methylene chloride
  7. customdried
  8. customevaporated in vacuo
  9. temperatureThe residue is heated
  10. temperatureat reflux in ethanolic hydrochloric acid overnight
  11. customThe volatiles are removed
  12. extractionNeutralization with ammonia and extraction with ethyl acetate

Sources & evidence

ORD record
ord-da4fd13ad0714b8d8388b58d795da03f
Source dataset
uspto-grants-1980_06
Patent number
US04206210

Reaction notes

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