Hydrochloric Acid → HCID 178422611, compound

HRID 1956172Notes

Reaction equation

HRID 1956172 reaction equation
C[S:2][C:3]1[C:8]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10]2([CH3:19])[CH3:18])=[CH:7][N:6]=[CH:5][N:4]=1.C[S-].[Na+].Cl>CN(C)C=O>[SH:2][C:3]1[C:8]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10]2([CH3:19])[CH3:18])=[CH:7][N:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 232269825-(2,2-Dimethyl-2,3-dihydro-1H-inden-1-yl)-4-(methylsulfanyl)pyrimidine

Product 1

HCID 178422611HCID 178422611, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (0.004 mol) of 4-methylthio-5-(2,2-dimethylindan-1-yl)pyrimidine and 1.4 g of sodium methanethiolate in 10 mL of N,N-dimethylformamide was prepared and heated to reflux with stirring for 1.5 hr. The mixture was cooled and was then added to 20 mL of 2N aqueous hydrochloric acid with stirring. The mixture obtained was extracted with 30 mL of ethyl acetate and the resulting organic solution was washed with water and then saturated aqueous sodium chloride. It was then dried over sodium sulfate and concentrated by evaporation under reduced pressure to obtain an oil. The oil was low pressure liquid chromatographed on silica gel eluting first with hexane to remove impurities and then with a 50:50 by volume mixture of ethyl acetate and hexane. The fractions containing the major component of the mixture were concentrated by evaporation under reduced pressure and the oil that was obtain solidified. The resulting 0.66 g (70 percent of theory) solids was the title compound melting at 184°-186° C.

Workup

  1. customwas prepared
  2. temperatureheated
  3. temperatureto reflux
  4. temperatureThe mixture was cooled
  5. stirringwith stirring
  6. customThe mixture obtained
  7. extractionwas extracted with 30 mL of ethyl acetate
  8. washthe resulting organic solution was washed with water
  9. dry with materialIt was then dried over sodium sulfate
  10. concentrationconcentrated by evaporation under reduced pressure
  11. customto obtain an oil
  12. customchromatographed on silica gel eluting first with hexane
  13. customto remove impurities
  14. additionwith a 50:50 by volume mixture of ethyl acetate and hexane
  15. additionThe fractions containing the major component of the mixture
  16. concentrationwere concentrated by evaporation under reduced pressure
  17. customthe oil that was obtain

Sources & evidence

ORD record
ord-0a6989c3c8c641c49c00bb1246f4bdd0
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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