Dimethylformamide → HCID 23289161, compound

HRID 366339Notes

Reaction equation

HRID 366339 reaction equation
CN(C)C=O.[Cl:6][C:7]1[C:12]2[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]([CH:16](Cl)[CH3:17])[O:15][C:11]=2[C:10]([N:24]2[C:29](=[O:30])[CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]([CH3:35])[C:25]2=[O:36])=[C:9]([F:37])[CH:8]=1.[C-:38]#[N:39].[K+].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:6][C:7]1[C:12]2[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]([CH:16]([C:38]#[N:39])[CH3:17])[O:15][C:11]=2[C:10]([N:24]2[C:29](=[O:30])[CH:28]=[C:27]([C:31]([F:33])([F:32])[F:34])[N:26]([CH3:35])[C:25]2=[O:36])=[C:9]([F:37])[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 23289174HCID 23289174, compound

Product 1

HCID 23289161HCID 23289161, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 ml of N,N-dimethylformamide was added to 0.8 g (1.6 mmol) of 3-[4-chloro-2-(1-chloroethyl)-3-ethoxycarbonyl-6-fluorobenzofuran-7-yl]-1-methyl-6-trifluoromethyluracil, 0.16 g (2.5 mmol) of potassium cyanide and 0.40 g (2.9 mmol) of potassium carbonate, followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, 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 0.58 g (yield: 74%) of the desired product as a yellow glassy substance. Refractive index: 1.5348 (20° C.).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water
  4. dry with materiala saturated sodium chloride aqueous solution and then, 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-6623c4fbcd2b44718b650016086afa03
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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