Dimethylformamide → HCID 21942316, compound

HRID 2216384Notes

Reaction equation

HRID 2216384 reaction equation
CN(C)C=O.Cl[C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[C:9]#[N:10].[CH2:18]([OH:23])[C:19]([CH3:22])([CH3:21])[CH3:20].[H-].[Na+]>O>[CH2:18]([O:23][C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[C:9]#[N:10])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6404Neopentyl alcoholHCID 24758Sodium hydrideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 21942316HCID 21942316, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide solution (364 ml) containing 2-chloro-5-nitrobenzonitrile (91 g) and neopentyl alcohol (52 g) was added sodium hydride (60% contained, 27.8 g) under ice-cooling, and the mixture was stirred for 1 hr. Water was added to the reaction mixture and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization and the crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give 2-neopentyloxy-5-nitrobenzonitrile (105 g). Subsequently, ammonium chloride (10 g) and iron powder (75 g) were added to a mixed solvent of water (286 ml) and ethanol (753 ml) and the mixture was heated to 65° C. 2-Neopentyloxy-5-nitrobenzonitrile (80.5 g) was added by portions over 20 min and the mixture was stirred at the refluxing temperature for 30 min. The reaction mixture was ice-cooled and filtrated. The solvent was evaporated under reduced pressure. An aqueous sodium hydroxide solution was added and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization and the crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (70 g). melting point: 55-56° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with toluene
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the residue
  7. customcrystallization
  8. customthe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-62793ce61d6545ac980f913fe167d859
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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