N-acetyl-2,3-dichlorophenacylamine → Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

HRID 703263Notes

Reaction equation

HRID 703263 reaction equation
C([NH:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[Cl:15])=[O:7])(=O)C>Cl>[ClH:14].[Cl:15][C:9]1[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:8]=1[C:6](=[O:7])[CH2:5][NH2:4]

Participants

3

Reactant 1

HCID 22151844N-acetyl-2,3-dichlorophenacylamine2×

Product 1

HCID 22151845Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

50.0 g of the N-acetyl-2,3-dichlorophenacylamine obtained in (a) are heated for 2 hours under reflux in 500 ml of hydrochloric acid. The slightly turbid reaction solution is concentrated by evaporation and the residue is digested with ethyl acetate. The crystalline 2,3-dichlorophenacylamine hydrochloride is isolated by filtration and dried. Melting point: 217°-218° C. IR (solid/KBr) in cm-1 : 1695 (CO). (Another crystal modification shows two carbonyl resonance bands at 1690 and 1705 cm-1). 1H-NMR (DMSO, d6) in ppm: 4.54 (s, 2H); 7.6 (t, 1H); 7.9 (m, 2H); 8.6 (s, 3H, replaceable with D2O).

Workup

  1. temperatureare heated for 2 hours
  2. concentrationThe slightly turbid reaction solution is concentrated by evaporation

Sources & evidence

ORD record
ord-2d666925c67e421a8de198d67073613e
Source dataset
uspto-grants-1991_01
Patent number
US04981990

Reaction notes

Loading…