ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 6.96 g (60 mmol) of sec-butyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 3 hours. The product was separated and then Kugelrohr distilled to yield 4.0 g of a colorless oil product (b.p.=100° C. @ 0.25 mm Hg) identified in Table I. The product was separated Kugelrohr distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 6.13 g (60 mmol) of n-propyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 18 hours. The product was separated and then recrystallized from n-heptane to yield 2.3 g of a yellow powder product (m.p.=33°-34° C.) identified in Table I. The product was separated recrystallized from n-heptane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 5.16 g (30 mmol) of n-octyl urea was reacted with 5.4 g (25 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 18 hours. The product was separated and then recrystallized from petroleum ether to yield 1.5 g of a white powder product (m.p.=36°-37° C.) identified in Table I. The product was separated recrystallized from petroleum ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 11.6 g (60 mmol) of adamantyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 24 hours. The product was separated and then recrystallized from methylcyclohexane to yield 7.0 g of a white solid product (m.p.=109°-111° C.) identified in Table I. The product was separated recrystallized from methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 8.52 g (60 mmol) of cyclohexyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 72 hours. The product was separated and then recrystallized several times from methylcyclohexane to yield 5.92 g of a fine white powder product (m.p.=73°-74° C.) identified in Table I. The product was separated recrystallized several times from methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 6 g (60 mmol) of allyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 18 hours. The product was separated and then recrystallized from methylcyclohexane to yield 4.77 g of a yellow solid product (m.p.=48°-49° C.) identified in Table I. The product was separated recrystallized from methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 7.0 g (60 mmol) of isobutyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 18 hours. The product was separated and then recrystallized from methylcyclohexane to yield 4.72 g of a yellow powder product (m.p.=43°-44° C.) identified in Table I. The product was separated recrystallized from methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 7.68 g (60 mmol) of cyclopentyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 18 hours. The product was separated and then recrystallized from methylcyclohexane to yield 5.0 g of a white solid product (m.p.=41°-42° C.) identified in Table I. The product was separated recrystallized from methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 8.2 g (60 mmol) of phenyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 24 hours. The product mixture was treated with methylene chloride, washed with water, dried and concentrated. The residue was recrystallized from methylcyclohexane to yield 6.2 g of crystal product (m.p.=114°-116° C.) identified in Table I. washed with water dried concentrated The residue was recrystallized from methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 4, 6.1 g (60 mmol) of isopropyl urea was reacted with 10.9 g (50 mmol) ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 24 hours. The product mixture was treated with methylene chloride, washed with water, dried and concentrated. The residue was recrystallized from methylcyclohexane to yield 6.3 g of crystal product (m.p.=51°-52° C.) identified in Table I. washed with water dried concentrated The residue was recrystallized from methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedures of Example 4, 5.3 g (60 mmol) of ethyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 24 hours. The product mixture was treated with methylene chloride, washed with water, dried and concentrated. The residue was recrystallized from methylcyclohexane to yield 8.0 g of crystal product (m.p.=89°-90° C.) identified in Table I. washed with water dried concentrated The residue was recrystallized from methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mechanically-stirred mixture of 53.2 g (0.885 mol) of urea and 38.6 g (0.177 mol) of ethyl α-chloro-γ,γ,γ-trifluoroacetoacetate was reacted in 50 ml dry dimethylformamide at 100°-110° C. for 71 hours. The reaction mixture was cooled to ambient temperature and the resulting orange slurry was poured into 500 ml of water and then cooled in an ice bath. Suction filtration of the mixture provided a mustard-colored solid material which when dried under an infrared lamp yielded 26.0 g of material. This solid material was slurried in hot chloroform, then cooled in an ice bath to yield 22.1 g of beige plate-like crystal material (m.p. 193-195° C.). A second crystal crop was obtained after concentration of the slurry residue, recrystallization in hot ether and filtration through glass wool. Total yield was 22.4 g of crystal product (m.p.=193°-195° C.) identified in Table 1. cooled in an ice bath Suction filtration of the mixture provided a mustard-colored solid material which when dried under an infrared lamp