2,2,3,3-tetrafluoropropanoyl chloride

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

Procedure: 5,6-Dichloro-2-amino-3-nitropyridine was prepared by chlorination of 5-chloro-2-amino-3-nitropyridine and was subsequently reacted with 2,2,3,3-tetrafluoropropionyl chloride. More particularly, 5,6-dichloro-2-amino-3-nitropyridine (3.0 grams; 0.15 mole) was taken up in tetrahydrofuran (20 ml.) and triethylamine (2 ml.) was added. Then 2,2,3,3-tetrafluoropropionyl chloride was added portionwise until all the starting material had reacted. The reaction yielded 5.3 grams (94 percent yield) of 5,6-dichloro-2-(2,2,3,3-tetrafluoropropionamido)-3-nitropyridine as an oil. Its identity was confirmed by infrared spectroscopy. had reacted

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

Procedure: 5-(Perfluorooctyl)-3-nitro-2-aminopyridine is reacted with 2,2,3,3-tetrafluoropropionyl chloride to obtain 5-(perfluorooctyl)-3-nitro-2-(2,2,3,3-tetrafluoropropionamido)pyridine, which when hydrogenated yields 6-(perfluorooctyl)-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine.

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

Procedure: 5-Chloro-3-nitro-2-aminopyridine is reacted with 2,2,3,3-tetrafluoropropionyl chloride to yield 5-chloro-3-nitro-2-(2,2,3,3-tetrafluoropropionamido)pyridine, which when hydrogenated yields 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine. This compound is reacted with trimethylamine to prepare 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine trimethylamine salt.

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

Procedure: 5-(Perfluorooctyl)-3-nitro-2-aminopyridine is reacted with 2,2,3,3-tetrafluoropropionyl chloride to obtain 5-(perfluorooctyl)-3-nitro-2-(2,2,3,3-tetrafluoropropionamido)pyridine, which when hydrogenated yields 6-(perfluorooctyl)-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine.

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

Procedure: 5-Chloro-3-nitro-2-aminopyridine is reacted with 2,2,3,3-tetrafluoropropionyl chloride to yield 5-chloro-3-nitro-2-(2,2,3,3-tetrafluoropropionamido)pyridine, which when hydrogenated yields 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo-(4,5-b)pyridine. This compound is reacted with trimethylamine to prepare 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo-(4,5-b)pyridine trimethylamine salt.

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

Procedure: 5-Chloro-3-nitro-2-aminopyridine is reacted with 2,2,3,3-tetrafluoropropionyl chloride to yield 5-chloro-3-nitro-2-(2,2,3,3-tetrafluoropropionamido)pyridine, which when hydrogenated yields 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo-(4,5-b)pyridine. This compound is reacted with trimethylamine to prepare 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo-(4,5-b)pyridine trimethylamine salt.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: With stirring and at 0° C., 25.0 g (152 mmol) of 3H-tetrafluoropropionyl chloride—dissolved in 20 ml dichloromethane—were added to a mixture of 14.4 g (182 mmol) of pyridine and 15.2 g (152 mmol) of butyl vinyl ether in 250 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. 250 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 12.5 g (36% of theory) of a yellowish oil. After the addition stirring the organic phase was separated off dried concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: With stirring and at 0° C., 25.0 g (152 mmol) of 3H-tetrafluoropropionyl chloride—dissolved in 20 ml dichloromethane—were added to a mixture of 14.4 g (182 mmol) of pyridine and 15.2 g (152 mmol) of butyl vinyl ether in 250 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. 250 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 12.5 g (36% of theory) of a yellowish oil. After the addition stirring the organic phase was separated off dried concentrated

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

Procedure: 5,6-Dichloro-2-amino-3-nitropyridine was prepared by chlorination of 5-chloro-2-amino-3-nitropyridine and was subsequently reacted with 2,2,3,3-tetrafluoropropionyl chloride. More particularly, 5,6-dichloro-2-amino-3-nitropyridine (3.0 grams; 0.15 mole) was taken up in tetrahydrofuran (20 ml.) and triethylamine (2 ml.) was added. Then 2,2,3,3-tetrafluoropropionyl chloride was added portionwise until all the starting material had reacted. The reaction yielded 5.3 grams (94 percent yield) of 5,6-dichloro-2-(2,2,3,3-tetrafluoropropionamido)-3-nitropyridine as an oil. Its identity was confirmed by infrared spectroscopy. had reacted

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

Procedure: 5-(Perfluorooctyl)-3-nitro-2-aminopyridine is reacted with 2,2,3,3-tetrafluoropropionyl chloride to obtain 5-(perfluorooctyl)-3-nitro-2-(2,2,3,3-tetrafluoropropionamido)pyridine, which when hydrogenated yields 6-(perfluorooctyl)-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine.

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

Procedure: 5-Chloro-3-nitro-2-aminopyridine is reacted with 2,2,3,3-tetrafluoropropionyl chloride to yield 5-chloro-3-nitro-2-(2,2,3,3-tetrafluoropropionamido)pyridine, which when hydrogenated yields 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine. This compound is reacted with trimethylamine to prepare 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine trimethylamine salt.

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

Procedure: 5-Chloro-3-nitro-2-aminopyridine is reacted with 2,2,3,3-tetrafluoropropionyl chloride to yield 5-chloro-3-nitro-2-(2,2,3,3-tetrafluoropropionamido)pyridine, which when hydrogenated yields 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine. This compound is reacted with trimethylamine to prepare 6-chloro-1-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-1H-imidazo(4,5-b)pyridine trimethylamine salt.