Dimethylformamide → HCID 20095263, compound

HRID 1770079Notes

Reaction equation

HRID 1770079 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([S:17][C:18]3[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:39]([O:45][CH2:46]Cl)(=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH2:46][O:45][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])=[O:15])=[C:12]([S:17][C:18]3[N:19]=[C:20]([O:26][CH3:27])[CH:21]=[C:22]([O:24][CH3:25])[N:23]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 20095262HCID 20095262, compound

Product 1

HCID 20095263HCID 20095263, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.70 g (0.0019 mol) of 4-(4-fluorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinic acid and 0.50 g (0.0036 mol) of potassium carbonate were weighed, and 10 ml of dimethylformamide was added thereto. The mixture was then stirred at room temperature for 1 hour. Thereafter, 0.34 g (0.0022 mol) of chloromethyl pivalate was further added to the resultant mixture, and the mixture was stirred at room temperature for 2 hours. The mixture was then poured into water, and was extracted with 50 ml of ethyl acetate. After washing with water and a saturated sodium chloride aqueous solution, it was dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel chromatography (developing solvent: ethyl acetate/hexane=1/4) to obtain 0.81 g of a yellowish thick syrup-like aimed product.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionwas extracted with 50 ml of ethyl acetate
  3. washAfter washing with water
  4. dry with materiala saturated sodium chloride aqueous solution, it was dried with anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by silica gel chromatography (developing solvent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-dd82cd46e6684a7a9e5c6aa9d4074c43
Source dataset
uspto-grants-1995_01
Patent number
US05385880

Reaction notes

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