HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Sulfite → Ethyl(6-((2,4-dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetate

HRID 591473
Notes
Print preview

Reaction equation

HRID 591473 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:14][C:9]=2S[CH:7]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[O-:37][S:38]([O-:40])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:10]2[CH:9]=[CH:14][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:12][C:11]=2[S:38](=[O:40])(=[O:37])[CH:7]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 118666999Ethyl(6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 71721636Ethyl(6-((2,4-dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetateYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Conditions

Temperature
25 °C

Procedure

To a mixture of ethyl(6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetate (10.0 g) in anhydrous DCM (400 mL) was added mCPBA (85%, 15.7 g), and the resulting solution was stirred at 25° C. for 3 d. To the reaction mixture was added Na2SO3 (30.0 g), and the mixture was stirred at 25° C. for 0.5 h. The reaction mixture was washed successively with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. The residue was washed with EtOAc to give the title compound (8.50 g).

Workup

  1. stirringthe mixture was stirred at 25° C. for 0.5 h
  2. washThe reaction mixture was washed successively with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with EtOAc

Sources & evidence

ORD record
ord-054e05d73d354d4b90f96785e676bf3d
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238639B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes