Ethanol → HCID 59161196, compound

HRID 545535Notes

Reaction equation

HRID 545535 reaction equation
C(Cl)(=O)C.C(O)C.Cl.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17]N)=[CH:13][CH:12]=1.O=[C:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:22][CH2:21]1>C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:16]=[C:15]2[C:14](=[CH:13][CH:12]=1)[NH:17][C:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:29])[CH3:30])[CH2:22][C:21]2=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6367Acetyl chlorideHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

Product 1

HCID 59161196HCID 59161196, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add acetyl chloride (8.5 mL, 120 mmol) to absolute ethanol (30 mL) and stir for 1 h. Add 4-methoxyphenylhydrazine hydrochloride (1.74 g, 10 mmol) and N-(4-oxo-cyclohexyl)-isobutyramide (Preparation 2) (1.83 g, 120 mmol) and reflux with stirring for 56 h. Cool to room temperature, dilute with ethyl acetate (100 mL) and wash with sodium bicarbonate solution (2×50 mL), and brine. Dry the organic portion(MgSO4), filter, and concentrate in vacuo. Dissolve in dichloromethane and pass over a silica pad, eluting with 20% ethyl acetate/dichloromethane. Obtain 2.32 g of a solid. Triturate the solid in diethyl ether with a small amount of dichloromethane, filter and dry under house vacuum to obtain 2.14 g (75%) of an off-white solid. MS (ES): m/z 287 (M+1)+, 285 (M−1)−; 1H NMR(DMSO-d6): δ 10.52 (s, 1H), 7.83 (d, 1H, J=7.5 Hz), 7.13 (d, 1H, J=8.8 Hz), 6.85 (s, 1H), 6.64 (dd, 1H, J=8.8, 2.2 Hz), 4.02 (m, 1H), 3.75 (m, 3H), 2.90 (dd, 1H, J=15.0, 5.3 Hz), 2.78 (m, 2H), 2.42 (m, 2H), 1.96 (m, 1H), 1.79 (m, 1H), 1.03 (d, 6H, J=6.6 Hz),

Workup

  1. stirringwith stirring for 56 h
  2. washwash with sodium bicarbonate solution (2×50 mL), and brine
  3. dry with materialDry the organic portion(MgSO4)
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. dissolutionDissolve in dichloromethane
  7. washpass over a silica pad, eluting with 20% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-51dda77e0fcb47f0a23804d0be4fda88
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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