Water → HCID 70292981, compound

HRID 366322Notes

Reaction equation

HRID 366322 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]=O)[O:10][C:6]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:4][CH:3]=1.[CH3:26][NH:27][NH2:28].O>O1CCCC1>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]=[N:28][NH:27][CH3:26])[O:10][C:6]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 23289186HCID 23289186, compound

Product 1

HCID 70292981HCID 70292981, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.4 g (1.0 mmol) of 3-(4-chloro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 5 ml of tetrahydrofuran, and 0.1 g (21.7 mmol) of monomethylhydrazine was added thereto under cooling with ice, 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 sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.2 g (yield: 47.6%) of the desired product as a pale yellow glassy substance. Refractive index: unmeasurable, 1H-NMR (solvent, CDCl3): 2.90(3H,s), 3.52(3H,s), 6.18(1H,bs), 6.40(1H,s), 6.85(1H,s), 7.05 (1H,d), 7.25(1H,s), 7.29(1H,d) ppm

Workup

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water
  5. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3f6520d8d6664872bb44620eb6cd6fa1
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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