2-Chloropropionyl chloride → 5-(1-Chloroethyl)-3-(3-chlorophenyl)-1,2,4-oxadiazole

HRID 732124Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[N:10][OH:11])[NH2:9])[CH:5]=[CH:6][CH:7]=1.[Cl:12][CH:13]([CH3:17])[C:14](Cl)=O>C(Cl)Cl>[Cl:12][CH:13]([C:17]1[O:11][N:10]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1)[CH3:14]

Participants

Conditions

Temperature: 120 °C

Procedure

1.80 g 3-chloro-N′-hydroxybenzenecarboximidamide and 3.7 mL DEA were dissolved under Ar in DCM (100 mL) and cooled on an ice/water bath, followed by addition of 2-chloropropanoyl chloride. After 1 h at r.t. the mixture was concentrated and the crude taken up in DMF (120 mL), followed by heating for at 120° C. for 2 h. The mixture was concentrated onto celite and purified via column chromatography (hep 100% to hep/EA=7/3) yielding the title compound (1.72 g, 67%). 1H NMR: 8.09 (t, 1 H), 7.93-8.02 (m, 1 H), 7.38-7.54 (m, 2 H), 5.22 (q, 1 H), 2.02 (d, 3 H)

Workup

temperaturecooled on an ice/water bath
concentrationAfter 1 h at r.t. the mixture was concentrated
concentrationThe mixture was concentrated onto celite
custompurified via column chromatography (hep 100% to hep/EA=7/3)

Sources & evidence

ORD record: ord-5dabda7e963d46a0abb1073286fc1600
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585881B2

Reaction notes

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