Ammonia → N-(2-Phenylpropan-2-yl)glycinamide

HRID 1283944Notes

Reaction equation

HRID 1283944 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]([CH3:14])([CH3:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[NH3:15]>C(O)C>[CH3:13][C:6]([NH:5][C:3](=[O:4])[CH2:2][NH2:15])([CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13142344HCID 13142344, compound

Product 1

HCID 21516969N-(2-Phenylpropan-2-yl)glycinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-N-(α,α-dimethylbenzyl)-acetamide (11.5 g; 0.054 mole) in ethanol (300 ml) was cooled to 0°C. The solution was saturated with ammonia (5 hours). Stirring was continued at room temperature for about 6 days. The solvent was removed under vacuum. The oily residue was taken up in 2N HCl and filtered. The filtrate was made alkaline by the addition of 2N NaOH. The alkaline phase was extracted three times with ether. The organic layer was dried over, anhydrous Na2SO4 and the solvent was evaporated. The N1 -(α,α-dimethylbenzyl)glycineamide was obtained as a light brown oil. Yield: 6.5 g (62.5 %).

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationfiltered
  3. additionby the addition of 2N NaOH
  4. extractionThe alkaline phase was extracted three times with ether
  5. dry with materialThe organic layer was dried over, anhydrous Na2SO4
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cab9a6b5a8b748b48da3e766d871f85a
Source dataset
uspto-grants-1976_08
Patent number
US03976771

Reaction notes

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