Dimethylformamide → HCID 14555602, compound

HRID 232255Notes

Reaction equation

HRID 232255 reaction equation
CN(C=O)C.[CH3:6][CH:7]([OH:16])[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[H-].[Na+].F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1>O>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([O:16][CH:7]([CH3:6])[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:21][CH:22]=1)([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 145556014-(morpholin-4-yl)butan-2-ol

Product 1

HCID 14555602HCID 14555602, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 mL of DMF is added α-methyl-4-morpholinepropanol (15.9 g, 0.1 mol) and 7.2 g (50% in mineral oil, 0.15 mol) of NaH followed by 14.1 g (0.1 mol) of 1-fluoro4-nitrobenzene. Heat the reaction at 80° C. and monitor the reaction by thin-layer chromatography. Upon completion of the reaction add 100 mL of water and extract with ether. Dry the organic phase over Na2SO4. Filter off the drying agent and evaporate the solvent in vacuo to obtain the title compound.

Workup

  1. temperatureHeat
  2. customthe reaction at 80° C.
  3. customthe reaction by thin-layer chromatography
  4. extractionextract with ether
  5. dry with materialDry the organic phase over Na2SO4
  6. filtrationFilter off the drying agent
  7. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-7e87870608ce441baafc14348908eac5
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Reaction notes

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