Hydrochloric Acid → HCID 18966277, compound

HRID 2226107Notes

Reaction equation

HRID 2226107 reaction equation
Br[C:2]1[C:7]2[O:8][C:9]([CH3:12])([CH3:11])[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])=[C:4]([F:26])[CH:3]=1.[Cu][C:28]#[N:29].CN(C)C=O.Cl>O>[C:28]([C:2]1[C:7]2[O:8][C:9]([CH3:11])([CH3:12])[O:10][C:6]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[N:15]([CH3:24])[C:14]2=[O:25])=[C:4]([F:26])[CH:3]=1)#[N:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 18966276HCID 18966276, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 18966277HCID 18966277, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

In a flask are placed 2.20 g (0.005 mole) of 3-(7-bromo-2,2-dimethyl-5-fluoro- 1,3-benzodioxol-4-yl)- 1 -methyl-6-trifluoromethyluracil, 0.62 g (0.0069 mole) of copper(I) cyanide and 60 mL of N,N-dimethylformamide. The resulting mixture is heated at reflux for 5 hours. This mixture is then cooled and poured into a solution of 2.5 g of hydrated ferric chloride, 0.62 mL of concentrated hydrochloric acid, and 3.8 mL of water. The resulting mixture is maintained at 60-70 ° C at which it is stirred for 20 minutes. After being cooled the mixture is extracted with methylene chloride, and the extract is washed with dilute hydrochloric acid. The extract is then dried over anhydrous magnesium sulfate, filtered, and the filtrate is evaporated under reduced pressure, leaving a residue. This residue is passed through a column of silica gel, eluting with ethyl acetate/heptane (1:1 ). The product-containing fractions are combined, and the solvent is evaporated under reduced pressure, leaving 3-(7-cyano-2,2-dimethyl-5-fluoro-1,3-benzodioxol-4-yl)-1-methyl-6-trifluoromethyluracil (Compound 15) as a residue.

Workup

  1. customIn a flask are placed
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for 5 hours
  4. temperatureThis mixture is then cooled
  5. temperatureAfter being cooled the mixture
  6. extractionis extracted with methylene chloride
  7. washthe extract is washed with dilute hydrochloric acid
  8. dry with materialThe extract is then dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate is evaporated under reduced pressure
  11. customleaving a residue
  12. washeluting with ethyl acetate/heptane (1:1 )
  13. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-2da016a8a4b74b9d9ee7d91cdf035300
Source dataset
uspto-grants-1994_09
Patent number
US05346881

Reaction notes

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