Ethanol → HCID 66739083, compound

HRID 1908706

Reaction equation

HRID 1908706 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])(=O)[CH3:12].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:31](O)[CH3:32]>>[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:9][C:11]([CH3:12])=[C:14]2[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:31][CH3:32])=[O:19]

Participants

6

Reactant 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 988106-Oxoheptanoic acidHCID 516892Sodium BicarbonateHCID 27239122-Bromophenylhydrazine hydrochloride

Product 1

HCID 66739083HCID 66739083, compound

Conditions

Temperature
50 °C

Procedure

To a solution of (2-bromophenyl)hydrazine hydrochloride (14 g) in ethanol (60 mL), 5-acetylvaleric acid (9.0 g) was added. The reaction mixture was stirred at 50° C. for 40 minutes, and concentrated sulfuric acid (6.0 mL) was added thereto, followed by heating under reflux for 16 hours. The reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution which was then extracted with ethyl acetate and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The resulting residue was purified by column chromatography (hexane:ethyl acetate=8:1) to obtain the title compound (15 g) having the following physical properties.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 16 hours
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe resulting residue was purified by column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-4295e18db1f149f794e3628bd88d7f26
Source dataset
uspto-grants-2013_12
Patent number
US08598223B2

Linked notes

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