Sodium Hydroxide → 7-(3,4-Methylenedioxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1277256Notes

Reaction equation

HRID 1277256 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+]>C(O)C.C1COCC1.Cl>[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 2

HCID 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 2

HCID 313Hydrochloric AcidSolventHCID 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 iN 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-2302db0de6d24a65b0a6252623b10bac
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

Loading…