Hydrochloric Acid → HCID 54303231, compound

HRID 442742Notes

Reaction equation

HRID 442742 reaction equation
[C:1]([CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])[N:8]=1)#[N:2].[C:17](=O)([O:20]C)[O:18][CH3:19].C[O-].[Na+].Cl>C1(C)C=CC=CC=1>[C:1]([CH:3]([C:4]1[S:5][CH:6]=[C:7]([C:9]2[C:10]([F:16])=[CH:11][CH:12]=[CH:13][C:14]=2[F:15])[N:8]=1)[C:17]([O:18][CH3:19])=[O:20])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 98134452-[4-(2,6-difluorophenyl)-1,3-thiazol-2-yl]acetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 54303231HCID 54303231, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2 g of 2-cyanomethyl-4-(2,6-difluorophenyl)thiazole and 4.8 g of dimethyl carbonate was added 30 ml of toluene, 0.6 g of sodium methoxide was added, and the resulting mixture was stirred and heated to the reflux temperature for 4 hours. After cooling, the reaction mixture was poured into 100 ml of ice-cold water, 1N-HCl was added to acidify the aqueous layer, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, and the residue obtained was purified by column chromatography (ethyl acetate/n-hexane=2/1) to give 1.67 g of methyl 2-cyano-2-{4-(2,6-difluorophenyl)thiazol-2-yl}acetate.

Workup

  1. additionwas added
  2. temperatureheated to the reflux temperature for 4 hours
  3. temperatureAfter cooling
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customthe residue obtained
  10. customwas purified by column chromatography (ethyl acetate/n-hexane=2/1)

Sources & evidence

ORD record
ord-87f0c55261304b98896429c1044e3d18
Source dataset
uspto-grants-1999_04
Patent number
US05891897

Reaction notes

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