((Chloromethyl)sulphonyl)benzene → HCID 21931738, compound

HRID 1244050Notes

Reaction equation

HRID 1244050 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([N+:14]([O-:16])=[O:15])[N:7]=1.Cl[CH2:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20].[K]>C1COCC1.CN(C=O)C>[C:22]1([S:19]([CH2:18][C:9]2[C:8]([N+:14]([O-:16])=[O:15])=[N:7][C:6]([CH:2]3[O:3][CH2:4][CH2:5][O:1]3)=[C:11]([O:12][CH3:13])[CH:10]=2)(=[O:21])=[O:20])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 81625((Chloromethyl)sulphonyl)benzeneHCID 5462222PotassiumHCID 21931671HCID 21931671, compound

Product 1

HCID 21931738HCID 21931738, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.6 g (2.6 mmol) 2-[1,3]dioxolan-2-yl-3-methoxy-6-nitro-pyridine, 0.55 g (2.9 mmol) of chloromethylphenylsulfone and 2.9 ml (2.9 mmol) of potassium t-butoxode (1M solution in THF) in 5 ml of DMF were combined at 5° C. and stirred at ambient temperature for 18 hours. The reaction mixture was quenched with 25 ml of water and extracted with ethyl acetate. The ethyl acetate extracts were combined, dried (Na2SO4), and evaporated. The residue was chromatographed on silica using 5:1 chloroform/ethyl acetate as the elutant. Appropriate fractions were combined and evaporated to yield 0.28 g of 3-benzenesulfonylmethyl-6-[1,3]dioxolan-2-yl-5-methoxy-2-nitro-pyridine as an oil. TLC: Rf=0.4 (1:1 chloroform/ethyl acetate). 1H NMR (CDCl3) δ 7.7 (m, 3H), 7.55 (m, 2H), 7.42 (s, 1H), 6.30 (s, 1H), 4.90 (s, 2H), 4.30 (m, 2H), 4.10 (m, 2H), 4.02 (s, 3H).). Mass Spectrum: m/e=381.0 (p+1).

Workup

  1. customwere combined at 5° C.
  2. customThe reaction mixture was quenched with 25 ml of water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica using 5:1 chloroform/ethyl acetate as the elutant
  7. customevaporated

Sources & evidence

ORD record
ord-9c57c199689947d28ea841786f3a097f
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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