Hydrochloric Acid → HCID 15477249, compound

HRID 366334Notes

Reaction equation

HRID 366334 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[C:4]([F:25])[CH:3]=1.[CH3:26][O:27]C(Cl)Cl.[Sn](Cl)(Cl)(Cl)Cl.Cl>ClCCl>[Cl:1][C:2]1[C:7]2[C:8]([CH:26]=[O:27])=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[N:14]([CH3:23])[C:13]2=[O:24])=[C:4]([F:25])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 15477207HCID 15477207, compound

Product 1

HCID 15477249HCID 15477249, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g (53 mmol) of 3-(4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 36.5 g (0.32 mol) of dichloromethyl methyl ether were dissolved in 100 ml of dichloromethane, and 200 ml (0.20 mol) of tin tetrachloride (1M dichloromethane solution) was dropwise added thereto at 0° C. After completion of the dropwise addition, stirring was carried out at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured into a mixture of dilute hydrochloric acid and ice and extracted with dichloromethane. The organic layer was washed with water 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 19.5 g (yield: 90.7%) of the desired product as white crystals. Melting point: 148-150° C.

Workup

  1. customat 0° C
  2. additionAfter completion of the dropwise addition
  3. customAfter completion of the reaction
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1b67856acf1146129789dd3ec4b30002
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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