Sodium hydride → (3-Dimethoxymethyl-4-nitro-phenyl)-morpholin-4-yl-phenyl-acetonitrile

HRID 390203

Reaction equation

HRID 390203 reaction equation
[H-].[Na+].[N:3]1([CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([CH:28]([O:31][CH3:32])[O:29][CH3:30])[CH:20]=1>CCCCCC.CN(C=O)C>[CH3:30][O:29][CH:28]([O:31][CH3:32])[C:21]1[CH:20]=[C:19]([C:9]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][CH2:8]2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]#[N:11])[CH:24]=[CH:23][C:22]=1[N+:25]([O-:27])=[O:26]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 85812Morpholino(phenyl)acetonitrileHCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzene

Product 1

HCID 58625101(3-Dimethoxymethyl-4-nitro-phenyl)-morpholin-4-yl-phenyl-acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

NaH (0.975 mol) was washed with hexane. After the hexane was decanted off, the NaH was stirred in DMF (1950 mL) at room temperature. Morpholin-4-yl-phenyl-acetonitrile (0.70 mol) in DMF (300 mL) was added dropwise under N2 gas. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was cooled in an ice bath and 4-chloro-2-dimethoxymethyl-1-nitrobenzene (0.86 mol) in DMF (150 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 2 hours and at room temperature overnight. The reaction mixture was poured on ice/water and extracted with diisopropyl ether. The organic layer washed with water, dried (MgSO4) and evaporated to yield the title compound as a solid.

Workup

  1. customAfter the hexane was decanted off
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. stirringThe reaction mixture was stirred at 0° C. for 2 hours and at room temperature overnight
  5. additionThe reaction mixture was poured on ice/water
  6. extractionextracted with diisopropyl ether
  7. washThe organic layer washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-1d31b37ec4e2482dbbf6c21164ab279f
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Linked notes

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