Water → HCID 21995720, compound

HRID 1978630Notes

Reaction equation

HRID 1978630 reaction equation
[CH2:1]([N:3]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[Br:16]N1C(=O)CCC1=O.O>CN(C=O)C.BrN1C(=O)CCC1=O>[Br:16][C:7]1[CH:6]=[CH:5][C:4]([N:3]([CH2:1][CH3:2])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH3:15])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 21995804HCID 21995804, compound

Product 1

HCID 21995720HCID 21995720, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 67184N-bromobutanimideCatalystHCID 6228DimethylformamideSolvent3×

Procedure

To a solution of N-ethyl-N-(2-propoxyethyl)aniline (10.18 g) in DMF (50 ml) was added at room temperature a solution of N-bromosuccinimide (7.45 g) in DMF (50 ml) for 40 minutes, and the mixture was stirred for 3 hours. To the mixture was added a solution of N-bromosuccinimide (0.2 g) in DMF (10 ml), and the mixture was stirred for 15 hours. The reaction mixture was added to water, and the mixture was extracted with diethylether. The organic layer was washed with water (twice) and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was distilled under reduced pressure (0.7 mmHg, 134° C.) to give pale yellow oil of 4-bromo-N-ethyl-N-(2-propoxyethyl)aniline (9.49 g).

Workup

  1. stirringthe mixture was stirred for 15 hours
  2. extractionthe mixture was extracted with diethylether
  3. washThe organic layer was washed with water (twice) and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. distillationthe residue was distilled under reduced pressure (0.7 mmHg, 134° C.)

Sources & evidence

ORD record
ord-1f1c87dd103548efb60121c080fe5cb2
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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