Hydrochloric Acid → HCID 22989969, compound

HRID 1169303Notes

Reaction equation

HRID 1169303 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][C:14]([C:20]([O:22]C)=[O:21])=[CH:13][C:12]=3[CH:24]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][C:14]([C:20]([OH:22])=[O:21])=[CH:13][C:12]=3[CH:24]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 22990199HCID 22990199, compound

Product 1

HCID 22989969HCID 22989969, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
67.5 °C

Procedure

Into a solution of methyl 7-[(4-chlorobenzyl)oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (200 mg) in THF/methanol (3/1.5 ml) was added at room temperature an aqueous solution (0.7 ml) of potassium carbonate (140 mg), and the resulting mixture was stirred at 65-70° C. for 23 hours. After cooling to room temperature, 1 N hydrochloric acid was added to the reaction mixture until the pH was adjusted to 5, and the precipitated crystals were collected by filtration. The crystals were washed with water, 2-propanol and diisopropyl ether to obtain 7-[(4-chlorobenzyl)oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (149 mg) as light yellow crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitated crystals were collected by filtration
  3. washThe crystals were washed with water, 2-propanol and diisopropyl ether

Sources & evidence

ORD record
ord-ea44edbf1a9a4837a1adfc5f6de9c8a0
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

Loading…