Water → HCID 23289179, compound

HRID 366326Notes

Reaction equation

HRID 366326 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11](O)[CH3:12])[O:10][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(Cl)C(=O)C([Cl:55])=C(Cl)C(=O)C=1Cl.O>C(#N)C>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]([Cl:55])[CH3:12])[O:10][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8371ChloranilHCID 11776TriphenylphosphineHCID 23289164HCID 23289164, compound

Product 1

HCID 23289179HCID 23289179, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.50 g (1.2 mmol) of 3-[4-chloro-2-(1-hydroxyethyl)-6-fluorobenzofuran-7-yl]-1-methyl-6-trifluoromethyluracil and 0.64 g (2.5 mmol) of triphenylphosphine were dissolved in 20 ml of acetonitrile, and 0.60 g (2.5 mmol) of chloranil was added thereto at room temperature. After stirring at room temperature for 2 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a 5% potassium carbonate aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.50 g (yield: 96.2%) of the desired product as a pale brown glassy substance. Refractive index: 1.5639 (20° C.).

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water
  4. dry with materiala 5% potassium carbonate aqueous solution and then dried over anhydrous sodium 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-393e531a68934716a8650b2ffa05d9c2
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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