CROTONAMIDE

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

Procedure: In substantially the same manner as in Reference Example 47, crotonamide was allowed to react with 1,3-dichloroacetone to give 4-chloromethyl-2-(1-propenyl)oxazole. The yield is 10%. Oily substance.

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

Procedure: Experimental Procedure: To a suspension of (E)-but-2-enamide (1.0 equiv) in 3.5 mL THF was added n-BuLi in hexanes (2.5 M,1.2 equiv) slowly at −78° C. The reaction mixture was warmed up to room temperature and stirred for 8 h before a solution of methacryloyl chloride (2.0 equiv) in 2 mL of THF was added drop wise at −78° C. The reaction mixture was allowed to warm up to rt overnight. The crude reaction mixture was diluted with ethyl acetate, and quenched with cold NH4Cl(aq, sat), and the organic layer separated. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. After filtration and evaporation under reduced pressure, the residue was purified by column chromatography to yield the pure compound. was added drop wise at −78° C to warm up to rt overnight The crude reaction mixture quenched with cold NH4Cl(aq, sat) the organic layer separated The aqueous layer was extracted twice with ethyl acetate The combined organic layers were washed with brine dried over MgSO4 After filtration and evaporation under reduced pressure the residue was purified by column chromatography to yield the pure compound

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

Procedure: In substantially the same manner as in Reference Example 47, crotonamide was allowed to react with 1,3-dichloroacetone to give 4-chloromethyl-2-(1-propenyl)oxazole. The yield is 10%. Oily substance.

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

Procedure: In substantially the same manner as in Reference Example 47, crotonamide was allowed to react with 1,3-dichloroacetone to give 4-chloromethyl-2-(1-propenyl)oxazole. The yield is 10%. Oily substance.

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

Procedure: To 200 ml of N,N-dimethylformamide, were added 17 g of crotonamide, 105 g of LEVATIT MP-500, which was also used in Example 68, and 32 g of benzylchloride. They were reacted at 50° C. for 4 hours with stirring. After the reaction, the reaction solution was treated in the same manner as in Example 69, the resulting distillation residue was recrystallized from benzine, and 25 of N-benzylcrotonamide having a melting point of 112.5°-113.6° C. was obtained (yield: 71%). They were reacted at 50° C. for 4 hours After the reaction the reaction solution was treated in the same manner as in Example 69 the resulting distillation residue was recrystallized from benzine, and 25 of N-benzylcrotonamide having a melting point of 112.5°-113.6° C. was obtained (yield: 71%)

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

Procedure: By replacing the crotonamide and the unsymmetrical-dimethylhydrazine employed in Example 38 by equimolar quantities of N-tert-butyl-3-(3-furfurylamino-4-chloro-5-methylsulfinylbenzoyloxy)crotonamide and unsymmetrical-diethylhydrazine respectively and then following substantially the same procedure described in Example 38 there is obtained 3-furfurylamino-4-chloro-5-methylsulfinylbenzoic acid 2,2-diethylhydrazide.

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

Procedure: Experimental Procedure: To a suspension of (E)-but-2-enamide (1.0 equiv) in 3.5 mL THF was added n-BuLi in hexanes (2.5 M,1.2 equiv) slowly at −78° C. The reaction mixture was warmed up to room temperature and stirred for 8 h before a solution of methacryloyl chloride (2.0 equiv) in 2 mL of THF was added drop wise at −78° C. The reaction mixture was allowed to warm up to rt overnight. The crude reaction mixture was diluted with ethyl acetate, and quenched with cold NH4Cl(aq, sat), and the organic layer separated. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. After filtration and evaporation under reduced pressure, the residue was purified by column chromatography to yield the pure compound. was added drop wise at −78° C to warm up to rt overnight The crude reaction mixture quenched with cold NH4Cl(aq, sat) the organic layer separated The aqueous layer was extracted twice with ethyl acetate The combined organic layers were washed with brine dried over MgSO4 After filtration and evaporation under reduced pressure the residue was purified by column chromatography to yield the pure compound

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

Procedure: In substantially the same manner as in Reference Example 47, crotonamide was allowed to react with 1,3-dichloroacetone to give 4-chloromethyl-2-(1-propenyl)oxazole. The yield is 10%. Oily substance.