Dichloroacetyl chloride → HCID 23087955, compound

HRID 2104436Notes

Reaction equation

HRID 2104436 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[Cl:14][CH:15]([Cl:19])[C:16](Cl)=[O:17]>C(OCC)(=O)C>[Cl:14][CH:15]([Cl:19])[C:16]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1)=[O:17]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 23087955HCID 23087955, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To 2-amino-5-fluoropyridine (250 mg) in ethyl acetate (10 mL), dichloroacetyl chloride (279 μL) was added at room temperature, followed by stirring at 60-70° C. for 2.5 hours. The reaction mixture was cooled, and saturated aqueous sodium hydrogencarbonate was added thereto for partitioning the mixture. The resultant organic layer was dried over magnesium sulfate anhydrate. The solvent was distilled away under reduced pressure, to thereby give the title compound (438 mg) as acrude product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customfor partitioning the mixture
  3. dry with materialThe resultant organic layer was dried over magnesium sulfate anhydrate
  4. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-304483f5a0ee4486994d1d62ea255a55
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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