Dimethyl Sulfoxide → HCID 15457072, compound

HRID 1385942Notes

Reaction equation

HRID 1385942 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[C:17]([CH:18]([OH:22])[CH2:19][CH2:20][CH3:21])=[CH:16][C:15]([C:23]2[C:24](=[O:34])[N:25]([CH3:33])[C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=2)=[C:14]([F:35])[CH:13]=1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[Cl:11][C:12]1[C:17]([C:18](=[O:22])[CH2:19][CH2:20][CH3:21])=[CH:16][C:15]([C:23]2[C:24](=[O:34])[N:25]([CH3:33])[C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=2)=[C:14]([F:35])[CH:13]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 15457071HCID 15457071, compound

Product 1

HCID 15457072HCID 15457072, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-65 °C

Procedure

0.21 g (1.64 mmol) of oxalyl chloride was dissolved in 10 ml of dichloromethane and cooled to −65° C. In a nitrogen atmosphere, 0.17 g (2.18 mmol) of dimethylsulfoxide was slowly dropwise added thereto, followed by stirring for 15 minutes. Then, 0.31 g (0.82 mmol) of 3-[4-chloro-2-fluoro-5-(1-hydroxybutyl)phenyl]-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 10 ml of dichloromethane and dropwise added thereto, followed by stirring for 1 hour. Further, 0.42 g (4.1 mmol) of triethylamine was dropwise added thereto, followed by heating to room temperature. An aqueous ammonium chloride solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.29 g (yield: 94%) of the desired product. 1H-NMR (300 MHz, CDCl3) σ value: 0.99(3H,t), 1.74(2H,sext), 2.94(2H,t), 3.70(3H,s), 6.78(1H,d), 7.25(1H,d), 7.53(1H,d), 7.75(1H,d)ppm.

Workup

  1. additiondropwise added
  2. stirringby stirring for 1 hour
  3. temperatureby heating to room temperature
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ebccecf828c64a22ac791d50284a451e
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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