2,6-Dimethylaniline → HCID 21312778, compound

HRID 971588Notes

Reaction equation

HRID 971588 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].Br[CH:11]([CH3:16])[CH2:12][O:13][CH2:14][CH3:15]>>[CH2:14]([O:13][CH2:12][CH:11]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9])[CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 68962,6-DimethylanilineHCID 2131277771385-98-3

Product 1

HCID 21312778HCID 21312778, compoundYield 46.1%

Procedure

Manufacture of the starting material: A solution of 484 g (4 mole) of 2,6-xylidine and 334 g (2 mole) of 2-bromo-1-ethoxypropane is cooled to 10° C. The reaction vessel is then evacuated to 13 mm Hg and the mixture heated at 130°-135° C. for 16 hours. After cooling 1 liter of diethylether and 1 liter of water are added to the mixture which is than made alkaline with 200 ml of a 30% sodium hydroxide solution. The ethereal phase is separated, washed with water until neutral, dried with sodium sulfate and evaporated in vacuo. 191.2 g of pure N-[1-ethoxyprop-2-yl]-2,6-dimethylaniline are obtained, b.p. 58°-62°/0.05 Torr.

Workup

  1. customThe reaction vessel is then evacuated to 13 mm Hg
  2. temperaturethe mixture heated at 130°-135° C. for 16 hours
  3. temperatureAfter cooling 1 liter of diethylether and 1 liter of water
  4. additionare added to the mixture which
  5. customThe ethereal phase is separated
  6. washwashed with water until neutral,
  7. dry with materialdried with sodium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a8a8a2b6042d425a9f63f1a3cd631dd7
Source dataset
uspto-grants-1979_07
Patent number
US04160660

Reaction notes

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