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

HRID 413595Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3S[CH2:19][CH2:18][C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][C:15]=3[CH:26]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].OO.[S:29]([O-:32])([O-])=[O:30].[Na+].[Na+].O>C(O)(=O)C>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[S:29](=[O:32])(=[O:30])[CH2:19][CH2:18][C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][C:15]=3[CH:26]=2)=[CH:9][CH:10]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 56 °C

Procedure

Ethyl 7-(4-propoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (15 g, 40.707 mmol) was suspended in 135 ml of acetic acid and was heated to 56° C. to dissolve. A solution of 30% hydrogen peroxide (9.5 g, 83.449 mmol) in 15 ml of acetic acid was dropped slowly and then was stirred at 65-70° C. for 3 hours. At that temperature, 60 ml of an aqueous sodium sulfite solution was dropped and disappearance of the peroxide was checked with iodo-starch paper. At that temperature, 15 ml of water was dropped. Crystals were formed and the mixture was cooled and stirred for 2 hours. After filtration, the residue was washed with 15 ml of a mixed solution of acetic acid/water =3/2 and subsequently with 150 ml of water. After vacuum drying (40° C.), 15.4 g (Yield 94%) of ethyl 7-(4-propoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate was obtained as white crystals.

Workup

dissolutionto dissolve
customCrystals were formed
temperaturethe mixture was cooled
stirringstirred for 2 hours
filtrationAfter filtration
washthe residue was washed with 15 ml of a mixed solution of acetic acid/water =3/2 and subsequently with 150 ml of water
customAfter vacuum drying (40° C.)

Sources & evidence

ORD record: ord-99506bfd133044ae88d3535cd70ecc1c
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566535B1

Reaction notes

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