Water → HCID 20512395, compound

HRID 894583Notes

Reaction equation

HRID 894583 reaction equation
P(Br)(Br)[Br:2].O[CH:6]([CH3:17])[CH2:7][NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16].O.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:2][CH:6]([CH3:17])[CH2:7][NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 136747711-(2,6-Dimethylanilino)propan-2-ol

Product 1

HCID 20512395HCID 20512395, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 250 ml (712 g, 2.63 moles) of phosphorous tribromide and 250 ml of dry chloroform is added dropwise to a solution of 100 g (0.558 moles) of N-(β-hydroxypropyl)-2,6-dimethyl-aniline in 500 ml of dry chloroform. During the addition the temperature of the mixture is maintained below +25° C. by cooling with icy water. The resulting mixture is boiled for 6 hours, thereafter it is cooled on salted ice, and 100 ml of water are added dropwise. The pH of the resulting mixture is adjusted to 9 with 10 n aqueous sodium hydroxide solutions. The phases are separated from each other, and the aqueous phase is extracted thrice with 300 ml of chloroform each. The organic solutions are combined, washed four times with 500 ml of water each, dried over anhydrous sodium sulfate, and the solvent is evaporated under reduced pressure. 118.2 g (87.5%) of N-(β-bromopropyl)-2,6-dimethyl-aniline are obtained as a colourless oily residue. This product is sufficiently pure to be applied directly in the next step. When distilling the oil at 0.3 mm Hg it boils at 102°-106° C.

Workup

  1. additionDuring the addition the temperature of the mixture
  2. temperatureis maintained below +25° C.
  3. additionare added dropwise
  4. customThe phases are separated from each other, and the aqueous phase
  5. extractionis extracted thrice with 300 ml of chloroform each
  6. washwashed four times with 500 ml of water each,
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-e1d67ca05ede44d8a40c7ade07a50bc4
Source dataset
uspto-grants-1981_08
Patent number
US04284642

Reaction notes

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