Thionyl Chloride → 3-(1-Chloroethyl)-5-(3-chlorophenyl)-[1,2,4]oxadiazole

HRID 732123Notes

Reaction equation

HRID 732123 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13](O)[CH3:14])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.O=S(Cl)[Cl:18]>CN(C=O)C>[Cl:18][CH:13]([C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:12][N:11]=1)[CH3:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 578379411-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol

Product 1

HCID 578379793-(1-Chloroethyl)-5-(3-chlorophenyl)-[1,2,4]oxadiazoleYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
70 °C

Procedure

5 drops of DMF were added to 1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethanol (12.3 g, 54.9 mmol) in SOCl2 (150 mL) and the reaction was heated at 70° C. for 5 h. The excess SOCl2 was evaporated and the residue was purified by column chromatography (Hep 100% to Hep/EA=5/1) to give 12.4 g (93%) of the title compound. 1H NMR: 1.96 (d, 3H) 5.20 (q, 1H) 7.46 (t, 1H) 7.59 (m, 1H) 8.04 (m, 1H) 8.17 (t, 1H)

Workup

  1. customThe excess SOCl2 was evaporated
  2. customthe residue was purified by column chromatography (Hep 100% to Hep/EA=5/1)

Sources & evidence

ORD record
ord-ede81e805f0143ce8c4c94ac5cc74b3b
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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