Sodium Bicarbonate → [4-(2,4-Dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-hydroxyphenyl]methanone

HRID 2411502Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][CH2:25][S:24]3(=[O:29])=[O:28])=[CH:19][C:18]=2[O:30]C)=[O:16])[CH2:11][CH2:10]1.ClCCl.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][CH2:25][S:24]3(=[O:29])=[O:28])=[CH:19][C:18]=2[OH:30])=[O:16])[CH2:13][CH2:14]1

Participants

Conditions

Temperature: -78 °C

Procedure

[4-(2,4-Dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methoxyphenyl]methanone (0.35 g) described in Example 89 was dissolved in dichloromethane (20 mL), 1 mol/L boron tribromide dichloromethane solution (4 mL) was added while stirring at −78° C. under cooling, and the mixture was stirred while rising the temperature to room temperature. Into the reaction mixture was poured ice water, and the mixture was neutralized with sodium hydrogen carbonate and extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (168 mg).

Workup

temperatureunder cooling
stirringthe mixture was stirred
customto room temperature
extractionextracted with chloroform
washThe organic layer was washed with saturated brine
customthe solvent was evaporated
customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record: ord-6d218dde807f4680835bb95e02bdcc2e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816079B2

Reaction notes

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