Dimethylformamide → HCID 18408334, compound

HRID 1385944Notes

Reaction equation

HRID 1385944 reaction equation
CN(C=O)C.[F:6][C:7]1[C:16]([C:17]2[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=2)=[CH:15][C:10]2[NH:11][C:12](=[O:14])[S:13][C:9]=2[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[C:36]#[CH:37]>O>[F:6][C:7]1[C:16]([C:17]2[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)=[CH:15][C:10]2[N:11]([CH2:37][C:36]#[CH:35])[C:12](=[O:14])[S:13][C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 18408326HCID 18408326, compound

Product 1

HCID 18408334HCID 18408334, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 10 ml of DMF, 0.4 g (1.2 mmol) of 3-(6-fluoro-benzothiazolin-2-on-5-yl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone, 0.18 g (1.3 mmol) of potassium carbonate and 0.15 g (1.3 mmol) of propargyl bromide were added, followed by heating and stirring at 70° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.32 g (yield: 72%) of the desired product. Melting point: 150-151° C. 1H-NMR (300 MHz, CDCl3) δ value: 2.30(1H,t), 3.73(3H,s), 4.73(2H,d), 6.80(1H,d), 7.27(1H,d), 7.45(1H,d), 7.56(1H,d)ppm.

Workup

  1. temperatureby heating
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe organic layer was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-14b60cc46c554dae8c8773a88092ef77
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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