Pyridine → HCID 13690971, compound

HRID 2290775Notes

Reaction equation

HRID 2290775 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:5]([C:7]1[O:11][N:10]=[C:9]([CH2:12][CH2:13]O)[N:8]=1)[CH3:6].S(Cl)([Cl:26])=O.N1C=CC=CC=1>C1C=CC=CC=1>[Cl:26][CH2:13][CH2:12][C:9]1[N:8]=[C:7]([CH:5]([CH3:6])[C:4]2[CH:15]=[CH:16][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:2]([F:1])[CH:3]=2)[O:11][N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 20230259HCID 20230259, compound

Product 1

HCID 13690971HCID 13690971, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.62 g of 5-(3-fluoro-4-phenyl-α-methylbenzyl)-3-(2-hydroxyethyl)-1,2,4-oxadiazole in 60 ml of dry benzene was successively added 2.0 g of thionyl chloride and 0.67 g of pyridine with ice-cooling. After stirring and heating with reflux for 1 hour, the reaction mixture was washed with water. The organic phase was further washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene to give 2.44 g of 3-(2-chloroethyl)-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole, m.p. 72°-72.5° C.

Workup

  1. temperaturecooling
  2. temperatureheating
  3. temperaturewith reflux for 1 hour
  4. washthe reaction mixture was washed with water
  5. washThe organic phase was further washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-efe5f6e3ab4143a381b0bf9432138082
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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