Chloroacetyl chloride → 2-(5-(Chloromethyl)-1,2,4-oxadiazol-3-yl)pyridine

HRID 2407747Notes

Reaction equation

HRID 2407747 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].O/[N:7]=[C:8](\[NH2:15])/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]1[O:4][N:15]=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 1354455062-Pyridylamidoxime

Product 1

HCID 151337662-(5-(Chloromethyl)-1,2,4-oxadiazol-3-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-chloroacetyl chloride (0.209 mL) in dichloromethane (3 mL) was added dropwise to a solution of (Z)—N′-hydroxypicolinamidine (0.300 g) in dichloromethane (7 mL). Triethylamine (0.366 mL) was added dropwise to the reaction solution and stirring at room temperature continued for 18 hours. The mixture was purified by column chromatography on silica gel (10-50% ethyl acetate in hexane). Desired fractions were evaporated in vacuo to a pale pink residue (0.21 g). This material was taken in toluene and refluxed for 18 hours. The solvent was evaporated in vacuo and the residue purified by column chromatography on silica gel (1-3% methanol in dichloromethane) to provide the title compound (0.085 g) having the following physical data.

Workup

  1. customThe mixture was purified by column chromatography on silica gel (10-50% ethyl acetate in hexane)
  2. customDesired fractions were evaporated in vacuo to a pale pink residue (0.21 g)
  3. temperaturerefluxed for 18 hours
  4. customThe solvent was evaporated in vacuo
  5. customthe residue purified by column chromatography on silica gel (1-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-2c8a92b687434152801a3e883dad9de1
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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