Acetic Anhydride → HCID 59239858, compound

HRID 1668374Notes

Reaction equation

HRID 1668374 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH2:13])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[OH-].[Na+].[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([NH:13][N:12]([C:9]1[CH:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=1)[C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])(=[O:25])[CH3:24]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 59239861HCID 59239861, compound

Product 1

HCID 59239858HCID 59239858, compound

Conditions

Temperature
90 °C

Procedure

tert-Butyl 1-[4-(ethoxycarbonyl)phenyl]hydrazinecarboxylate (5.60 g) and acetic anhydride (10 ml) were mixed, and the mixture was stirred at 90° C. for 1 hr. The reaction mixture was neutralized with 1N aqueous sodium hydroxide solution, and washed with water and saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 (volume ratio)→1:1 (volume ratio)), and further recrystallized from ethyl acetate-hexane to give the title compound (4.42 g) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane
  5. customethyl acetate=19:1 (volume ratio)→1:1 (volume ratio)), and further recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0be8f64e73cb4e06a62096cdb94d78e8
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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