Potassium Carbonate → HCID 13747728, compound

HRID 648941Notes

Reaction equation

HRID 648941 reaction equation
[CH3:1][C:2]([C:5]1[N:6]=[C:7]([C:10]2[CH2:11][CH2:12][N:13](CC3C=CC=CC=3)[CH2:14][CH:15]=2)[S:8][CH:9]=1)([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].C(OC(Cl)=O)=C>ClCCCl>[CH3:4][C:2]([C:5]1[N:6]=[C:7]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)[S:8][CH:9]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78808Vinyl chloroformateHCID 13747806HCID 13747806, compound

Product 1

HCID 13747728HCID 13747728, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5.5 g 4-(4-(1,1-dimethylethyl)-2-thiazolyl)-1-phenylmethyl-1,2,3,6-tetrahydropyridine, 2.5 g K2CO3 and 50 ml 1,2-dichloroethane are treated dropwise at -10° to -7° under stirring with 3.75 ml chloroformic acid vinyl ester. The mixture is stirred at -10° to -7° for 3 hours. The solvent is evaporated, the residue partitioned between water and hexane, and the water phase extracted with hexane. The combined organic layers are washed with saturated brine solution, filtered and dried (Na2SO4). The solvent is evaporated and the oily residue is added under ice-cooling to 20% aqueous hydrochloric acid. The mixture is heated on a steam bath for 4 hours, then cooled to room temperature and extracted once with dichloromethane. The aqueous acidic solution is filtered, made alkaline with aqueous NaOH and extracted with ethyl ether. After evaporation of ether, the heading compound is obtained as an oily residue. M.p. of the hydrogenmaleinate is 170°-171°.

Workup

  1. customThe solvent is evaporated
  2. customthe residue partitioned between water and hexane
  3. extractionthe water phase extracted with hexane
  4. washThe combined organic layers are washed with saturated brine solution
  5. filtrationfiltered
  6. dry with materialdried (Na2SO4)
  7. customThe solvent is evaporated
  8. additionthe oily residue is added under ice-
  9. temperaturecooling to 20% aqueous hydrochloric acid
  10. temperatureThe mixture is heated on a steam bath for 4 hours
  11. extractionextracted once with dichloromethane
  12. filtrationThe aqueous acidic solution is filtered
  13. extractionextracted with ethyl ether
  14. customAfter evaporation of ether
  15. customthe heading compound is obtained as an oily residue
  16. customis 170°-171°

Sources & evidence

ORD record
ord-97b40a4fdb194b90a4c0d66b26b23c6f
Source dataset
uspto-grants-1988_04
Patent number
US04737500

Reaction notes

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