Water → HCID 23289160, compound

HRID 366331Notes

Reaction equation

HRID 366331 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][OH:12])[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.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].O>O1CCCC1>[C:33]([O:12][CH2:11][C:9]1[O:10][C:6]2[C:5]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=2[CH:8]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23289198HCID 23289198, compound

Product 1

HCID 23289160HCID 23289160, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.4 g (1.1 mmol) of 3-(4-chloro-2-hydroxymethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 0.13 g (1.2 mmol) of triethylamine were dissolved in 20 ml of tetrahydrofuran, and 0.1 g (1.2 mmol) of acetyl chloride was dropwise added thereto under cooling with ice. After completion of the reaction, the reaction solution was poured into water and washed with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, 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 0.2 g (yield: 45.5%) of the desired product as white solid. Melting point: 135-138° C.

Workup

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. washwashed with ethyl acetate
  4. washThe organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water
  5. dry with materiala saturated sodium chloride aqueous solution, and then, dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-60f2d8d8e19c465ba9cb501b214e604e
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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