Toluene → 2-[3-(Chloromethyl)-1,2,4-oxadiazol-5-yl]pyridine

HRID 420433Notes

Reaction equation

HRID 420433 reaction equation
[Cl:1][CH2:2][C:3](=[N:5][OH:6])[NH2:4].C(Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[N:10][CH:9]=1.[C:15]1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:1][CH2:2][C:3]1[N:4]=[C:15]([C:9]2[CH:8]=[CH:13][CH:12]=[CH:11][N:10]=2)[O:6][N:5]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 183583-(Chloromethyl)pyridineHCID 41122522-chloro-N'-hydroxyethanimidamide

Product 1

HCID 162282342-[3-(Chloromethyl)-1,2,4-oxadiazol-5-yl]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Step-1: To the stirred solution of 2-chloroacetamidoxime (1.0 g, 9.2 mmol, prepared as per the procedure given in PCT/US02/22897) in toluene (15 ml) was added nicotinyl chloride (1.37 g, 9.67 mmol) and heated at 110° C. for 4 hr. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with aqueous saturated sodium bicarbonate solution (2×25). Organic layer was evaporated under vacuum to yield the crude product. The crude product was purified using silica gel column chromatography (15% Acetone-Hexane) to give 2-(3-chloromethyl-[1,2,4]-oxadiazole-5-yl)-pyridine in 55% (0.550 g) yield. MS: m/z: 196.7 (M+1).

Workup

  1. washwashed with aqueous saturated sodium bicarbonate solution (2×25)
  2. customOrganic layer was evaporated under vacuum
  3. customto yield the crude product
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-371b512a97684df8b2e9c8f341ab1688
Source dataset
uspto-grants-2012_01
Patent number
US08097594B2

Reaction notes

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