Dimethylformamide → HCID 21942316, compound

HRID 1744489Notes

Reaction equation

HRID 1744489 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>[N+:15]([C:12]1[CH:13]=[CH:14][C:7]([O:23][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:8]([CH:11]=1)[C:9]#[N:10])([O-:17])=[O:16]

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 dimethylformamide solution (364 ml) containing 2-chloro-5-nitrobenzonitrile (91 g) and neopentyl alcohol (52 g) was added sodium hydride (60% content, 27.8 g) under ice-cooling and the mixture was stirred for 1 h. The reaction mixture was poured into water and extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give 5-nitro-2-neopentyloxybenzonitrile (105 g), melting point: 90–91° C.

Workup

  1. temperaturecooling
  2. extractionextracted with toluene
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the 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-e85cba1755dc411c920115fbc298d02a
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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