Triethylamine → 5,6-Dichloro-2-(2,2,3,3-tetrafluoropropionamido)-3-nitropyridine

HRID 371674Notes

Reaction equation

HRID 371674 reaction equation
ClC1C=C([N+]([O-])=O)C(N)=NC=1.[F:12][C:13]([F:20])([CH:17]([F:19])[F:18])[C:14](Cl)=[O:15].[Cl:21][C:22]1[CH:23]=[C:24]([N+:30]([O-:32])=[O:31])[C:25]([NH2:29])=[N:26][C:27]=1[Cl:28].C(N(CC)CC)C>O1CCCC1>[Cl:21][C:22]1[CH:23]=[C:24]([N+:30]([O-:32])=[O:31])[C:25]([NH2:29])=[N:26][C:27]=1[Cl:28].[Cl:21][C:22]1[CH:23]=[C:24]([N+:30]([O-:32])=[O:31])[C:25]([NH:29][C:14](=[O:15])[C:13]([F:20])([F:12])[CH:17]([F:19])[F:18])=[N:26][C:27]=1[Cl:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2241682-Amino-5-chloro-3-nitropyridineHCID 27767442,2,3,3-Tetrafluoropropanoyl chloride2×HCID 153920475,6-Dichloro-3-nitropyridin-2-amine

Product 2

HCID 153920475,6-Dichloro-3-nitropyridin-2-amineHCID 203554865,6-Dichloro-2-(2,2,3,3-tetrafluoropropionamido)-3-nitropyridineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customhad reacted

Sources & evidence

ORD record
ord-b73a1749fe3d4ae39de37129aa3e7e93
Source dataset
uspto-grants-1978_05
Patent number
US04087432

Reaction notes

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