Potassium Carbonate → HCID 21284141, compound

HRID 2232016Notes

Reaction equation

HRID 2232016 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.[Cl:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[OH:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:8][C:6]1[CH:7]=[C:2]([O:24][C:15]2[CH:16]=[CH:17][C:18]([C:20]([F:21])([F:22])[F:23])=[CH:19][C:14]=2[Cl:13])[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27366032-Chloro-4-(trifluoromethyl)phenolHCID 18922464Methyl 4,6-dichloropyridine-2-carboxylate

Product 1

HCID 21284141HCID 21284141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture consisting of 2.06 gm (0.01 mol) of methyl 4,6-dichloro-picolinate, 2.15 gm (0.011 mol) of 2-chloro-4-trifluoromethyl-phenol, 1.5 gm of pulverized potassium carbonate and 5 ml of dimethylformamide was heated at 120° C. for one hour, while stirring. The mixture solidified. The solid mass was stirred and decanted several times with ice water, then acidified with acetic acid, and finally extracted with ethyl acetate. The organic phase was separated, washed with water and dried with sodium sulfate. The solvent was distilled off, and the residual oil was purified by chromatography on 40 gm of silicagel (eluant: Diisopropyl ether). 1.4 gm (38% of theory) of the title compound were obtained as a virtually colorless oil. Rf -value: 0.48 (prepared thin-layer chromatography plates manufactured by E. Merck, Darmstadt, Germany, with silicagel 60-F-254. Eluant: Acetone/diisopropyl ether 1:2; the spots are visible in ultraviolet light at 254 μm).

Workup

  1. stirringThe solid mass was stirred
  2. customdecanted several times with ice water
  3. extractionfinally extracted with ethyl acetate
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialdried with sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residual oil was purified by chromatography on 40 gm of silicagel (eluant: Diisopropyl ether)

Sources & evidence

ORD record
ord-73dc9a4619274bc190c2e4f61a6b4fd5
Source dataset
uspto-grants-1988_11
Patent number
US04786317

Reaction notes

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