Propylene Oxide → HCID 13674776, compound

HRID 1164436Notes

Reaction equation

HRID 1164436 reaction equation
S(Cl)([Cl:3])=O.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].CC1C=CC=C(C)C=1N.O1C(C)C1.[OH-].[Na+]>C1C=CC=CC=1.O>[Cl:3][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

8

Reactant 5

HCID 6378Propylene OxideHCID 68962,6-DimethylanilineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 136747711-(2,6-Dimethylanilino)propan-2-ol

Product 1

HCID 13674776HCID 13674776, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 123 ml (202 g, 1.7 moles) of thionyl chloride in 200 ml of dry benzene is added dropwise to a solution of 100 g (0.558 moles) of N-(β-hydroxypropyl)-2,6-dimethyl-aniline (prepared from 2,6-dimethylaniline and 1,2-epoxipropane as described in the published Dutch patent application No. 6,507,312; b.p.: 120°-125° C./1 mm Hg; yield: 51%) in 1000 ml of dry benzene at room temperature under nitrogen atmosphere. The resulting mixture is stirred and boiled under nitrogen atmosphere for 5 hours. The mixture is cooled with icy water, 100 ml of water are added dropwise to the cooled mixture, and the pH of the resulting mixture is adjusted to 9 with 10 n aqueous sodium hydroxide solution. The phases are separated from each other, and the aqueous phase is extracted thrice with 200 ml of benzene each. The organic solutions are combined, washed thrice with 300 ml of water each, dried over anhydrous sodium sulfate, and the solvent is evaporated under reduced pressure. The residual dark brown oil is divided into two parts of about equal weights, and then distilled under reduced pressure. 85 g (77%) of N-(β-chloropropyl)-2,6-dimethyl-aniline are obtained as a colourless oil boiling at 105°-108° C./0.8 mm Hg.

Workup

  1. customat room temperature
  2. additionare added dropwise to the cooled mixture
  3. customThe phases are separated from each other, and the aqueous phase
  4. extractionis extracted thrice with 200 ml of benzene each
  5. washwashed thrice with 300 ml of water each,
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-34978ef10be349f8bc20ae5cc2cb92ca
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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