Carbon Tetrachloride → 2-(Chloromethyl)-5-(1,2-oxazol-3-yl)pyridine

HRID 2101412

Reaction equation

HRID 2101412 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)[Cl:14].ClN1C(=O)CCC1=O>CCOC(C)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:14][CH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 31398Chlorosuccinimide2×HCID 598348122-Methyl-5-(1,2-oxazol-3-yl)pyridine

Product 1

HCID 598348302-(Chloromethyl)-5-(1,2-oxazol-3-yl)pyridineYield 34%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring mixture of 3-(6-methylpyridin-3-yl)isoxazole (76 mg, 0.474 mmol) and 6 mL carbon tetrachloride, was added N-chlorosuccinimide (69.7 mg, 0.52 mmol), followed by 3 mg benzoyl peroxide. The reaction mixture was refluxed. Additional N-chlorosuccinimide (40 mg, 0.30 mmol) was added in two portions after stirring 2 h and 4 h. After refluxing for a total of 13 h the reaction mixture was diluted with EtOAc, then washed sequentially with 1 N aq. NaOH solution, water and brine. The organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes) to isolate 31 mg (34%) of the title compound as a white solid. HPLC/MS: retention time=1.77 min, [M+H]+=195.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperatureAfter refluxing for a total of 13 h the reaction mixture
  3. washwashed sequentially with 1 N aq. NaOH solution, water and brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-aba49369da18458998d184dd12aa8a6b
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Linked notes

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