Sulfuric Acid → α-Amino-2,4-dichlorobenzeneacetamide

HRID 849969Notes

Reaction equation

HRID 849969 reaction equation
S(=O)(=O)(O)O.[NH2:6][CH:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])[C:8]#[N:9].[OH2:18].N>O>[NH2:6][CH:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])[C:8]([NH2:9])=[O:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12896473Azane;hydrateHCID 16783112HCID 16783112, compound

Product 1

HCID 19365492α-Amino-2,4-dichlorobenzeneacetamideYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 11.2 g of concentrated sulfuric acid was added to 0.54 g of water, to which 10.1 g of 2-amino-2-(2,4-dichlorophenyl)acetonitrile was added under ice cooling, and the mixture was heated at 50° to 60° C. under stirring for 3 hours. After completion of the reaction, the reaction mixture was poured into 30 ml of concentrated ammonia water cooled with ice in such a manner that the temperature of the solution became not higher than 20° C. The precipitated crystals were collected by filtration, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was combined with the previously collected crystals, followed by recrystallization, which afforded 6.14 g (yield, 57%) of 2-amino-2-(2,4-dichlorophenyl)acetamide, m.p. 113.8° C.

Workup

  1. additionwas added under ice cooling
  2. temperaturethe mixture was heated at 50° to 60° C.
  3. customAfter completion of the reaction
  4. temperaturecooled with ice in such a manner that the temperature of the solution
  5. custombecame not higher than 20° C
  6. filtrationThe precipitated crystals were collected by filtration
  7. extractionthe filtrate was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated sodium chloride solution
  9. dry with materialdried with anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customfollowed by recrystallization, which

Sources & evidence

ORD record
ord-784b17ea7d73421c8e953a4099dc965f
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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