Acetic Acid → 8-Chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one-6-oxide

HRID 366778Notes

Reaction equation

HRID 366778 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.C(O)(=[O:20])C>>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[C:7]3[C:12]([CH2:13][S:14](=[O:20])[C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 152802298-Chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one

Product 1

HCID 232898988-Chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one-6-oxide

Procedure

A solution of 8-chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one (250 mg) in acetic acid (5 ml) was stirred for 5 minutes. NaBO3 (105 mg) was added and the mixture was stirred for 7 hours. The reaction was quenched with 5% NaOH and extracted with CH2Cl2, and the extracts were washed with brine, dried (MgSO4), filtered and concentrated to afford a tan solid (270 mg). This was chromatographed on silica to afford the crude sulfoxide (250 mg) as a tan solid containing some starting material; MS (CI, M+H)=278.

Workup

  1. customThe reaction was quenched with 5% NaOH
  2. extractionextracted with CH2Cl2
  3. washthe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f52d9e001ecd49b6a0f6c8c83d5b7c1d
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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