Diisopropylethylamine → HCID 67279279, compound

HRID 1694639Notes

Reaction equation

HRID 1694639 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:5]=[C:6]([CH2:8][N:9]=NO)[CH:7]=1.Cl[CH:17](C)[C:18](Cl)=[O:19].C([N:25](C(C)C)CC)(C)C.Cl[CH2:32][Cl:33].CN(C)C=O>>[Cl:33][CH2:32][CH2:17][C:18]1[O:19][N:25]=[C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([C:12]([F:13])([F:14])[F:15])[CH:5]=2)[N:9]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 1110192-Chloropropionyl chlorideHCID 22350042dichloromethane N,N-dimethylformamideHCID 178526386HCID 178526386, compound

Product 1

HCID 67279279HCID 67279279, compound

Procedure

To a solution of [5-fluoro-3-(trifluoromethyl)phenyl](hydroxyimino)-methylamine (8.884 g, 40 mmol) in a mixture of anhydrous dichloromethane/N,N-dimethylformamide (60/20 ml) was added 2-chloropropanoyl chloride (6.0 ml, 58.7 mmol) and diisopropylethylamine (14.0 ml, 80.3 mmol), and the mixture was stirred at room temperature for two hours. The mixture was then refluxed overnight with stirring, cooled to room temperature, and solvent removed under reduced pressure. The residue was fractionally distilled under vacuum, and the portion boiling at 95-105° C./0.8-1.0 mm Hg retained, to provide 5-(chloroethyl)-3-[5-fluoro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole as a yellow oil, MS 295.1 (M+H).

Workup

  1. temperatureThe mixture was then refluxed overnight
  2. stirringwith stirring
  3. temperaturecooled to room temperature
  4. customsolvent removed under reduced pressure
  5. distillationThe residue was fractionally distilled under vacuum

Sources & evidence

ORD record
ord-1bd422047af5473ba248bbe88434f1e0
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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