Sulfuric Acid → HCID 19365490, compound

HRID 849968Notes

Reaction equation

HRID 849968 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[F: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[F:17])[C:8]([NH2:9])=[O:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12896473Azane;hydrateHCID 19365528α-Amino-4-chloro-2-fluorobenzeneacetonitrile

Product 1

HCID 19365490HCID 19365490, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 20 g of concentrated sulfuric acid was added to 1.03 g of water, to which 17 g of 2-amino-2-(4-chloro-2-fluorophenyl)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 100 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 15.3 g (yield, 82%) of 2-amino-2-(4-chloro-2-fluorophenyl)acetamide.

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-de0d3d40581e4a998349dabb7a1531e8
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

Loading…