1,2-Dichloroethane → HCID 118020438, compound

HRID 1747511Notes

Reaction equation

HRID 1747511 reaction equation
C(Cl)CCl.[CH3:5][NH:6][CH3:7].[Cl:8][C:9]1[N:14]=[C:13]([C:15](O)=[O:16])[C:12]([C:18]([F:21])([F:20])[F:19])=[CH:11][CH:10]=1.[Cl-].[NH4+]>ClCCl>[Cl:8][C:9]1[N:14]=[C:13]([C:15]([N:6]([CH3:7])[CH3:5])=[O:16])[C:12]([C:18]([F:21])([F:20])[F:19])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 25517Ammonium ChlorideHCID 112990916-chloro-3-(trifluoromethyl)pyridine-2-carboxylic Acid

Product 1

HCID 118020438HCID 118020438, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDC (650 mg, 3.39 mmol) and dimethylamine (2.0 M solution in THF, 2.30 mL, 4.60 mmol) were added at room temperature to a solution of 6-chloro-3-(trifluoromethyl)pyridine-2-carboxylic acid (516 mg, 2.29 mmol) in dichloromethane (20 mL), and the mixture was stirred at room temperature for 4 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with dichloromethane. The obtained organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-70/30 (gradient)] to obtain the title compound (246 mg, yield: 43%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe obtained organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-70/30 (gradient)]

Sources & evidence

ORD record
ord-c060cde2355f4a79b0555b9bd6f48ba0
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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