Chloroform → HCID 15457064, compound

HRID 1385939Notes

Reaction equation

HRID 1385939 reaction equation
C(Cl)(Cl)Cl.[Cl:5][C:6]1[C:11]([S:12](Cl)(=[O:14])=[O:13])=[CH:10][C:9]([C:16]2[C:17](=[O:27])[N:18]([CH3:26])[C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)=[C:8]([F:28])[CH:7]=1.Cl.CN.[CH2:32]([N:34](CC)CC)C>O>[Cl:5][C:6]1[C:11]([S:12](=[O:14])(=[O:13])[NH:34][CH3:32])=[CH:10][C:9]([C:16]2[C:17](=[O:27])[N:18]([CH3:26])[C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)=[C:8]([F:28])[CH:7]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 15457058HCID 15457058, compound

Product 1

HCID 15457064HCID 15457064, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 25 ml of chloroform, 0.6 g (1.5 mmol) of 3-(4-chloro-5-chlorosulfonyl-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone and 1.8 g (26.7 mmol) of methylamine hydrochloride were added, and 6.0 g (59.4 mmol) of triethylamine was dropwise added thereto under cooling with ice, followed by stirring at room temperature for 2 hours. This reaction solution was poured into water and extracted with chloroform. After washing with water and a 10% citric acid aqueous solution, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.4 g (yield:67) of the desired product. Melting point: 150-151° C.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with chloroform
  3. washAfter washing with water
  4. dry with materiala 10% citric acid aqueous solution, the organic layer was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c9b0937b700e4fc7b2a81c6aacf66802
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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