Chlorodifluoromethane → HCID 68780083, compound

HRID 2266442Notes

Reaction equation

HRID 2266442 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8](=[O:26])[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[C:10]([CH3:17])[NH:11]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH:35]([F:37])[F:36]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:26][CH:35]([F:37])[F:36])=[C:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:10]([CH3:17])=[N:11]2

Participants

5

Reactant 3

HCID 6372Chlorodifluoromethane2×HCID 11430Potassium CarbonateHCID 68782520HCID 68782520, compound

Product 1

HCID 68780083HCID 68780083, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of [8-chloro-3-(4-chlorobenzyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (0.080 g), N,N-dimethylformamide (2.0 mL) and potassium carbonate (0.080 g) at −80° C. was added chlorodifluoromethane (0.4 mL). The flask was sealed and the resulting mixture warmed to room temperature and then stirred at this temperature for 17 hours. The excess chlorodifluoromethane was allowed to evaporate and the residue diluted with water and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound as a light brown solid, 0.10 g.

Workup

  1. customThe flask was sealed
  2. customto evaporate
  3. additionthe residue diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fcf5de67f8e746ca99a2dfd1139c541a
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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