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N-methyl-2-pyrrolidone → 3-Chloro-2-isopropylsulfonyl-1-nitrobenzene

HRID 1879637
Notes
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Reaction equation

HRID 1879637 reaction equation
[CH:1]([S:4]([O-:6])=[O:5])([CH3:3])[CH3:2].[Na+].CN1CCCC1=O.Cl[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]>O>[Cl:22][C:21]1[C:16]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 185552,3-DichloronitrobenzeneHCID 23685748Sodium propane-2-sulfinate

Product 1

HCID 574541743-Chloro-2-isopropylsulfonyl-1-nitrobenzeneYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of sodium isopropylsulfinate (3.3 g) and N-methyl-2-pyrrolidinone (20 mL), 2,3-dichloronitrobenzene (4 g) was added and stirred overnight at 70° C. The reaction mixture was diluted with water, and the precipitated solid was collected by filtration and washed with diethyl ether to give 3-chloro-2-isopropylsulfonyl-1-nitrobenzene (3.0 g) as a white solid.

Workup

  1. additionwas added
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-13d5fda60e4d4100b3cdfdeaab8f0bcc
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318702B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes