Ammonia → HCID 10081732, compound

HRID 1856298Notes

Reaction equation

HRID 1856298 reaction equation
Br[CH:2]([CH3:15])[C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:13][CH3:14])=[O:4].[NH3:16]>>[NH2:16][CH:2]([CH3:15])[C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:13][CH3:14])=[O:4]

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 439233653984-87-5

Product 1

HCID 10081732HCID 10081732, compound

Conditions

Temperature
55 °C

Procedure

A slurry of 20.9 g 2-bromo-2'-ethyl-6'-methyl propionanilide, 125 ml 95% alcohol, and 75 ml concd. ammonia was saturated with gaseous ammonia and was heated to 55° C. for 30 hours in a pressure vessel. The reaction mixture was filtered and the filtrate concentration in vacuo. The residue was dissolved in 2M hydrochloric acid and was extracted with ethyl acetate. The acid phase was made alkaline to pH 9 and was extracted with methylene chloride to give 15.5 g of a crystallizing oil. Recrystallized from ether-petroleum ether, the compound (2-amino-2'-ethyl-6'-methylpropionanilide) melted at 68.5°-70° C. Calcd. for C12H18N2O: C 69.8, H 8.79, N 13.6. Found: C 69.7, N 8.72, N 13.5.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentration in vacuo
  3. dissolutionThe residue was dissolved in 2M hydrochloric acid
  4. extractionwas extracted with ethyl acetate
  5. extractionwas extracted with methylene chloride

Sources & evidence

ORD record
ord-fdc84165a83b412a8268fe94de344e64
Source dataset
uspto-grants-1980_08
Patent number
US04218477

Reaction notes

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