Dimethylformamide → HCID 22227856, compound

HRID 1744523Notes

Reaction equation

HRID 1744523 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].[CH:18]1([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[H-].[Na+]>O>[CH:18]1([O:24][C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[C:9]#[N:10])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 22227856HCID 22227856, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dimethylformamide solution (35 ml) containing 2-chloro-5-nitrobenzonitrile (14.1 g) and cyclohexanol (8.5 g) was added sodium hydride (60% content, 3.7 g) under ice-cooling, and the mixture was stirred for 1 h. The reaction mixture was added to water and extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether to give 2-cyclohexyloxy-5-nitrobenzonitrile (11.6 g), melting point: 97–98° C.

Workup

  1. temperaturecooling
  2. extractionextracted with toluene
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customafter which the solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-edd8c23c554a4a2cb35a5ec126ce1b41
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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