Hydrochloric Acid → 7-(3,4-Methylenedioxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1388012Notes

Reaction equation

HRID 1388012 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:11]=[CH:12][C:13]4[S:19][CH2:18][CH2:17][C:16]([C:20]([O:22]C)=[O:21])=[CH:15][C:14]=4[CH:24]=3)=[CH:4][C:3]=2[O:2]1.[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:11]=[CH:12][C:13]4[S:19][CH2:18][CH2:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:14]=4[CH:24]=3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18472255Methyl 7-(3,4-methylenedioxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 184724237-(3,4-Methylenedioxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 88.8%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of methyl 7-(3,4-methylenedioxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (0.6 g) in ethanol/THF (10/10 ml) was added at room temperature 1N sodium hydroxide solution (2 ml), and the mixture was stirred for 64 hours. To the mixture was added 1N hydrochloric acid (3 ml), and the mixture was concentrated, The resulting solid was collected by filtration, which was washed with water, 2-propanol and diisopropylether to give pale yellow powder of 7-(3,4-methylenedioxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acid (510.6 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. filtrationThe resulting solid was collected by filtration, which
  3. washwas washed with water, 2-propanol and diisopropylether

Sources & evidence

ORD record
ord-6c833da4333547c495140224eb858627
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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