Water → HCID 21957948, compound

HRID 2213591Notes

Reaction equation

HRID 2213591 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=O)[CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[CH2:16](Br)[CH2:17]CC.O>CN(C)C=O>[CH2:11]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)[CH2:12][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 258025N-[4-(Propan-2-yl)phenyl]ethanimidic acid

Product 1

HCID 21957948HCID 21957948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-isopropylphenyl)acetamide (1.8 g) in dimethylformamide (18 mL) was added, under ice-cooling, 60% sodium hydride (0.44 g). Further, butyl bromide (1.4 mL) was added and the mixture was stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed, dried and concentrated under reduced pressure. 4N Hydrochloric acid (13 mL) was added to the residue and the mixture was refluxed for 7 hr. Water was added to the reaction mixture followed by neutralization and the mixture was extracted with ethyl acetate. The organic layer was washed, dried and concentrated under reduced pressure to give butyl(4-isopropylphenyl)amine (1.8 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. addition4N Hydrochloric acid (13 mL) was added to the residue
  7. temperaturethe mixture was refluxed for 7 hr
  8. additionWater was added to the reaction mixture
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed
  11. customdried
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ecdafcd2ed5b4599974a2b4e68310f25
Source dataset
uspto-grants-2006_09
Patent number
US07105567B2

Reaction notes

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