Thionyl Chloride → 2-(2,2-Difluoroethyl)oxy-5-nitro-nicotinic acid chloride

HRID 1846090Notes

Reaction equation

HRID 1846090 reaction equation
[F:1][CH:2]([F:17])[CH2:3][O:4][C:5]1[N:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:6]=1[C:7](O)=[O:8].S(Cl)([Cl:20])=O>CN(C=O)C.C(Cl)Cl>[F:1][CH:2]([F:17])[CH2:3][O:4][C:5]1[N:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:6]=1[C:7]([Cl:20])=[O:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 866586692-(2,2-Difluoroethyl)oxy-5-nitro-nicotinic acid

Product 1

HCID 584834192-(2,2-Difluoroethyl)oxy-5-nitro-nicotinic acid chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2,2-difluoroethyl)oxy-5-nitro-nicotinic acid (310 mg, 1.25 mmol), 2.0 mL thionyl chloride, 5.0 mL DCM and one drop of DMF was refluxed for 4 h and concentrated i.vac. The corresponding acid chloride was directly used for the next step without further purification.

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationconcentrated i.vac
  3. customThe corresponding acid chloride was directly used for the next step without further purification

Sources & evidence

ORD record
ord-1f85543b08c14a02b58e6c42104df552
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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