Hydrochloric Acid → 7-(4-Methoxyphenyl)-2,3-dihydro-1-benzo-thiepine-4-carboxylic acid

HRID 1277252Notes

Reaction equation

HRID 1277252 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[S:18][CH2:17][CH2:16][C:15]([C:19]([O:21]C)=[O:20])=[CH:14][C:13]=3[CH:23]=2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[S:18][CH2:17][CH2:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][C:13]=3[CH:23]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18472336Methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 184723977-(4-Methoxyphenyl)-2,3-dihydro-1-benzo-thiepine-4-carboxylic acidYield 106.2%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (0.50 g) in ethanol/THF (10/10 ml) was added at room temperature 1N sodium hydroxide solution (2 ml), and the mixture was stirred for 18 hours. To the mixture was added 1N hydrochloric acid (2 ml). Under reduced pressure, the mixture was concentrated. To the mixture was added water, and the precipitates were collected by filtration, which were washed with 2-propanol, diethylether and hexane to give pale yellow solid of 7-(4-methoxyphenyl)-2,3-dihydro-1-benzo-thiepine-4-carboxylic acid (508 mg). This compound was used for the following reaction, without subjecting further purification.

Workup

  1. concentrationUnder reduced pressure, the mixture was concentrated
  2. additionTo the mixture was added water
  3. filtrationthe precipitates were collected by filtration, which
  4. washwere washed with 2-propanol, diethylether and hexane

Sources & evidence

ORD record
ord-b036e853607d428b847b7d94578fba98
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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