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

HRID 2411502
Notes
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Reaction equation

HRID 2411502 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 71252392[4-(2,4-Dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methoxyphenyl]methanone

Product 1

HCID 71252235[4-(2,4-Dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-hydroxyphenyl]methanoneYield 49.6%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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

  1. temperatureunder cooling
  2. stirringthe mixture was stirred
  3. customto room temperature
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes