Ammonia → HCID 22765668, compound

HRID 1576137Notes

Reaction equation

HRID 1576137 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>C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[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

5

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 1

HCID 11192Zinc AcetateCatalyst

Procedure

19.57 g. (0.1 moles) of 2-(p-chloro-phenoxy)- 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 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 of 23.6 g. (yield 88%), mp.: 98°-100°C/0.02 mmHg. The distilled product crystallizes after standing for 48 hours, Mp. 59°-61°C.

Workup

  1. customat a temperature of 140°-150°C
  2. temperaturethe mixture is cooled
  3. dissolutiondissolved in 300 ml
  4. washof chloroform and the solution washed with water to neutral reaction
  5. dry with materialAfter drying the solution over anhydrous magnesium sulphate it
  6. customis evaporated to dryness
  7. distillationThe green-yellow colored oil (26.5 g.), is subjected to fractional distillation in vacuo
  8. customThe distilled product crystallizes
  9. waitafter standing for 48 hours

Sources & evidence

ORD record
ord-80ed68a5ff6c4ac8b059a5db2b7e93f7
Source dataset
uspto-grants-1976_09
Patent number
US03979405

Reaction notes

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