Water → (+/-)-2-chloroacetamide N-methyl-2-phenylacetamide

HRID 915516Notes

Reaction equation

HRID 915516 reaction equation
N[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([NH:5][CH3:6])=[O:4].O.C([O-])([O-])=O.[Na+].[Na+].[Cl:20]CC(Cl)=O>CC(C)=O>[Cl:20][CH2:2][C:3]([NH2:5])=[O:4].[CH3:6][NH:5][C:3](=[O:4])[CH2:2][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chloride2×HCID 10340Sodium Carbonate2×HCID 145848722-amino-N-methyl-2-phenylacetamide

Product 1

HCID 69109715(+/-)-2-chloroacetamide N-methyl-2-phenylacetamideYield 83.55%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

Compound (II) obtained in the previous example (395.0 g, 2.405 mol) and acetone (1074 mL) were placed in a 5 L glass reactor and deionised water (1303 mL) was added to the slightly cloudy resulting solution, with a slight exothermic reaction of 6° C. being observed. Then, Na2CO3 (153.0 g, 1.443 mol) was added, with a slight exothermic reaction of 2° C. being observed. The resulting whitish suspension was cooled with an ice water bath at 0°-5° C. and, for approximately 1 hour without exceeding 5° C., a solution made up of chloroacetyl chloride (III) (201.0 mL, 285.3 g, 2.526 mol) in acetone (735 mL) was slowly added. The addition created vapours and a slight release of gases. The resulting milky suspension was stirred at 0°-5° C. and, after 1.5 hours, Na2CO3 (30.6 g, 0.289 mol) and a solution made up of chloroacetyl chloride (38.3 mL, 54.3 g, 0.481 mol) in acetone (140 mL) was added. After a further 1.5 hours, the suspension was concentrated at reduced pressure to a volume of approximately 1.0 L, with approximately 3.0 L having been distilled. The white thick suspension was cooled to 18°±2° C. and was filtered, with the filter being washed with deionised water (300 mL). A white solid was obtained that was dried at 60° C. and at reduced pressure and, which corresponded to the title product (I), having a melting point of 192-194° C. (483.7 g, 83.55% yield).

Workup

  1. customwere placed in a 5 L glass reactor
  2. temperatureThe resulting whitish suspension was cooled with an ice water bath at 0°-5° C. and, for approximately 1 hour
  3. customwithout exceeding 5° C.
  4. additionwas slowly added
  5. additionThe addition
  6. additionwas added
  7. waitAfter a further 1.5 hours
  8. concentrationthe suspension was concentrated at reduced pressure to a volume of approximately 1.0 L, with approximately 3.0 L
  9. distillationhaving been distilled
  10. temperatureThe white thick suspension was cooled to 18°±2° C.
  11. filtrationwas filtered, with the filter
  12. washbeing washed with deionised water (300 mL)
  13. customA white solid was obtained
  14. customthat was dried at 60° C. and at reduced pressure and, which

Sources & evidence

ORD record
ord-d7769f216300495db3281193ddfb55a7
Source dataset
uspto-grants-2007_09
Patent number
US07265223B2

Reaction notes

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