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Acetic Acid → (6-Methoxy-3-nitro-2-pyridinyl)methyl phenyl sulfone

HRID 731570
Notes
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Reaction equation

HRID 731570 reaction equation
CC([O-])(C)C.[K+].[C:7]1([S:13]([CH2:16]Cl)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=1.C(O)(=O)C>O1CCCC1>[CH3:18][O:19][C:20]1[N:21]=[C:22]([CH2:16][S:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:15])=[O:14])[C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 795252-Methoxy-5-nitropyridineHCID 81625((Chloromethyl)sulphonyl)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 13902761(6-Methoxy-3-nitro-2-pyridinyl)methyl phenyl sulfoneYield 80%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A 1 M KOt-Bu solution in tetrahydrofuran (50 mL, 50 mmol) is cooled to −40° C., treated portion-wise with a solution of chloromethyl phenyl sulfone (4.39 g, 23.0 mmol) and then with a solution of 2-methoxy-5-nitropyridine (3.55 g, 23.0 mmol) in tetrahydrofuran, stirred for 45 min at −40° C., treated with glacial acetic acid (3.0 g, 50 mmol) and filtered. The filtercake is air-dried to give the title compound as a tan solid, 5.70 g (80% yield), mp 147-149° C., identified by mass spectral and HNMR analyses.

Workup

  1. filtrationfiltered
  2. customThe filtercake is air-dried

Sources & evidence

ORD record
ord-96090cd68d904704b46e3ea011558c57
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07585873B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes