Ammonia → HCID 22765668, compound

HRID 1111857Notes

Reaction equation

HRID 1111857 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][C:7]([CH3:11])([CH3:10])[C:8]#[N:9])=[CH:4][CH:3]=1.N[C:15]([CH3:19])([CH3:18])[CH2:16][OH:17].N>[Zn].C([O-])(=O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][C:7]([C:8]2[O:17][CH2:16][C:15]([CH3:19])([CH3:18])[N:9]=2)([CH3:10])[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 118072-Amino-2-methyl-1-propanolHCID 27813212-(4-chlorophenoxy)-2-methylpropanenitrile

Product 1

HCID 22765668HCID 22765668, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 15671365HCID 15671365, compoundCatalystHCID 6212ChloroformSolvent

Procedure

19.57 g (0.1 moles) of 2-(p-chlorophenoxy)-2-methyl-propionitrile are reacted under stirring for 34 hours with 17.83 g (0.2 moles) of 2-amino-2-methyl-1-propanol in the presence of 0.66 g (0.003 moles) of zinc-acetate catalyst at a temperature of 140°-150° C. The reaction takes place under an intensive development of ammonia gas. When the gas development is finished, the mixture is cooled, dissolved in 300 ml of chloroform and the solution washed with water to neutral reaction. After drying the solution over anhydrous magnesium sulphate, it is evaporated to dryness. The green-yellow colored oil (26.5 g) is subjected to fractional distillation in vacuo. The main fraction is a product 2-[(p-chlorophenoxy)-isopropyl]-4,4-dimethyl-2-oxazoline of 23.6 g (yield 88%), m.p.: 98°-100° C./0.02 mmHg. The distilled product crystallizes after standing for 48 hours, m.p.: 59°-61° C.

Workup

  1. temperaturethe mixture is cooled
  2. washthe solution washed with water to neutral reaction
  3. dry with materialAfter drying the solution over anhydrous magnesium sulphate, it
  4. customis evaporated to dryness
  5. distillationThe green-yellow colored oil (26.5 g) is subjected to fractional distillation in vacuo
  6. customThe distilled product crystallizes

Sources & evidence

ORD record
ord-b4e2506824954a3a9a9d990c6348af99
Source dataset
uspto-grants-1978_10
Patent number
US04119633

Reaction notes

Loading…