Carbon Dioxide → HCID 19889059, compound

HRID 653576Notes

Reaction equation

HRID 653576 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]2[N:14]=[C:15]([SH:17])[N:16]=[C:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:24][C:25](I)([F:27])[F:26].C(=O)=O>CN(C)C=O.C(Cl)Cl.C(OCC)(=O)C.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]2[N:14]=[C:15]([S:17][C:25]([F:27])([F:26])[F:24])[N:16]=[C:4]2[N:3]=1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 16843TrifluoroiodomethaneHCID 178422622HCID 178422622, compound

Product 1

HCID 19889059HCID 19889059, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
30 °C

Procedure

To 1.5 g (6.2 mmol) of 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-thiol and 1.5 g (10.9 mmol) of powdered potassium carbonate stirring in 20 ml of dimethylformamide, 3 ml of condensed trifluoromethyl iodide was added dropwise at ambient temperature. Keeping the dry ice condenser on from the addition, the stirred mixture was warmed to 30° C. At three separate times during a 2 h period, 2.0 ml portions of trifluoromethyliodide were added. Excess water was added and the aqueous mixture was extracted with a 1:1 mixture of ethyl acetate/diethyl ether (200 ml) and the organic layer was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oil. Silica gel column chromatography (methylene chloride followed by 1:1 methylene chloride/ethyl acetate) afforded 0.4 g of the title compound (main component present), m.p. 91°-93° C.

Workup

  1. additionwas added dropwise at ambient temperature
  2. additionon from the addition
  3. customAt three separate times during a 2 h period, 2.0 ml portions of trifluoromethyliodide
  4. additionwere added
  5. additionExcess water was added
  6. extractionthe aqueous mixture was extracted with a 1:1 mixture of ethyl acetate/diethyl ether (200 ml)
  7. washthe organic layer was washed with water, saturated sodium bicarbonate, brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customto give an oil

Sources & evidence

ORD record
ord-6ef7ac1ae29e4fdc944015fa5ef7f4a0
Source dataset
uspto-grants-1992_07
Patent number
US05127936

Reaction notes

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