Hydrogen Peroxide → Ethyl 7-(4-propoxyethoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxlate

HRID 413602Notes

Reaction equation

HRID 413602 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3S[CH2:22][CH2:21][C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][C:18]=3[CH:29]=2)=[CH:10][CH:9]=1)[CH2:2][CH3:3].OO.[S:32]([O-:35])([O-])=[O:33].[Na+].[Na+].O>C(O)(=O)C>[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[S:32](=[O:35])(=[O:33])[CH2:22][CH2:21][C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][C:18]=3[CH:29]=2)=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 24437Sodium SulfiteHCID 70034579Ethyl 7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 70033921Ethyl 7-(4-propoxyethoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxlateYield 94.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

Ethyl 7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (45 g, 109.1 mmol) was suspended in 405 ml of acetic acid and was heated to 60° C. to dissolve. A solution of 30% hydrogen peroxide (25.35 g, 223.6 mmol) in 45 ml of acetic acid was dropped slowly at 60-70° C. After the dropping, the mixture was stirred at 65-70° C. for 3 hours. At that temperature, 40 ml of an aqueous sodium sulfite solution was dropped and disappearance of the peroxide was checked with iodo-starch paper. After dropping 275 ml of water at that temperature, the mixture was cooled and stirred for 2 hours and then was stirred at 0-10° C. for 30 minutes. After filtration, the residue was washed with an ice-cooled, mixed solution of acetic acid/water (45 ml/31.5 ml) and subsequently with 225 ml of water. After vacuum drying (40° C.), 45.9 g (Yield 94.6%) of ethyl 7-(4-propoxyethoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate was obtained as white crystals.

Workup

  1. dissolutionto dissolve
  2. temperaturethe mixture was cooled
  3. stirringstirred for 2 hours
  4. stirringwas stirred at 0-10° C. for 30 minutes
  5. filtrationAfter filtration
  6. washthe residue was washed with an ice-
  7. temperaturecooled
  8. additionmixed solution of acetic acid/water (45 ml/31.5 ml)
  9. customAfter vacuum drying (40° C.)

Sources & evidence

ORD record
ord-cdb3fdd8630e488fa6d96f9668dedc53
Source dataset
uspto-grants-2003_05
Patent number
US06566535B1

Reaction notes

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