Potassium Carbonate → HCID 22990028, compound

HRID 1169480Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (400 mg), 3-methoxybenzyl chloride (350 mg) and potassium carbonate (412 mg) were suspended in DMF (15 ml), and the resulting suspension was stirred at 60° C. for 13 hours. The reaction mixture was diluted with ethyl acetate and washed respectively with water and an aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate. After concentration under reduced pressure to remove the solvent, the residue was subjected to purification using silica gel column chromatography (hexane:ethyl acetate=4:1-hexane:ethyl acetate=3:1) to obtain methyl 7-(3-methoxybenzyloxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (459 mg) as a light yellow, amorphous substance.

Workup

washwashed respectively with water
dry with materialan aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate
concentrationAfter concentration under reduced pressure
customto remove the solvent
customthe residue was subjected to purification

Sources & evidence

ORD record: ord-c9cba9c47c0540939500e248ce148552
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627651B1

Reaction notes

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