2-Acetylcyclohexanone → HCID 18614772, compound

HRID 1265181Notes

Reaction equation

HRID 1265181 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([Cl:22])[C:13]=1[NH:23][NH2:24]>CCO>[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:15]=[C:14]([Cl:22])[C:13]=1[N:23]1[C:1]([CH3:2])=[C:4]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[N:24]1

Participants

4

Reactant 2

HCID 134002-AcetylcyclohexanoneHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 18614772HCID 18614772, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetylcyclohexanone (0.12 mL, 1 mmol) and 2,6-dichloro-4-trifluoromethylphenylhydrazine (245 mg, 1 mmol) in EtOH (10 mL) was heated under reflux for 12 hr. EtOH was removed under reduced pressure and the product purified by flash chromatography on silica (10% EtOAc:Hexane): yield 67%. 1H NMR (CDCl3) δ 7.8 (s, 2H), 2.7 and 2.05 (m, 2H each), 2.05 (s, 3H), 1.9 (m, 4H); MS (M+) 349.

Workup

  1. temperatureunder reflux for 12 hr
  2. customEtOH was removed under reduced pressure
  3. customthe product purified by flash chromatography on silica (10% EtOAc:Hexane)

Sources & evidence

ORD record
ord-ab34848051924e73a6d9155ac5db1162
Source dataset
uspto-grants-2003_04
Patent number
US06545033B1

Reaction notes

Loading…