Nitrogen → HCID 20447335, compound

The intermediate N-[2'-chloro-5'-trifluoromethylphenyl]-3-chloro-4-chloromethyl-2-pyrrolidinone is prepared as follows: 50 g of 2-chloro-5-trifluoromethylaniline is combined with 34.8 g of triethylamine (TEA) and 200 ml of CH2Cl2. 48.6 g of dichloroacetyl chloride (DCAC) added dropwise while the mixture was kept at about 10° C. The mixture was stirred overnight forming a precipitate. The mixture was brought up to 1800 ml with CH2Cl2 and was washed 3 times (×) with 300 ml water, 3×300 ml 1.0N HCL and 3×300 ml saturated NaHCO3. The precipitate was dried over night with magnesium sulfate (MgSO4) and stripped, yielding 59 g of 2'-chloro-5'-trifluoromethyldichloroacetanilide. 58.3 g of the 2'-chloro-5'-trifluoromethyldichloroacetanilide and 37.2 g of potassium carbonate (K2CO3) were combined with 300 ml acetone and heated with stirring to reflux in a 2 liter flask equipped with a thermal reflux condenser, drop funnel and N2 bubbler. 39.1 g allyl bromide was added via the drop funnel at a constant temperature at 60° C. The mixture was refluxed for 2 hours and then stirred overnight. The mixture was filtered and stripped. 200 ml CH2Cl2 was added to the residue. This mixture was washed 3× with 100 ml H2O and 2× with 100 saturated NaCl solution. The filtrate was dried overnight in MgSO4 and stripped to yield 55 g of N-allyl-2'-chloro-5'-trifluoromethyldichloroacetanilide.

1. temperatureheated
2. temperatureto reflux in a 2 liter flask
3. customequipped with a thermal reflux condenser, drop funnel
4. temperatureThe mixture was refluxed for 2 hours
5. stirringstirred overnight
6. filtrationThe mixture was filtered
7. addition200 ml CH2Cl2 was added to the residue
8. washThis mixture was washed 3× with 100 ml H2O and 2× with 100 saturated NaCl solution
9. dry with materialThe filtrate was dried overnight in MgSO4

ORD record

ord-6643b8f74ca0403d8ae347621dca96c5

Source dataset

uspto-grants-1984_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04469701