Pyridine → HCID 19822291, compound

HRID 1030233Notes

Reaction equation

HRID 1030233 reaction equation
N1C=CC=CC=1.[C:7]([C:11]1[C:12](=[O:22])[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[C:19](=O)[CH:20]=1)([CH3:10])([CH3:9])[CH3:8].[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>ClC(Cl)C.O1CCCC1.O.[Ti](Cl)(Cl)(Cl)Cl>[C:7]([C:11]1[CH:20]=[C:19]([NH:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12]=1[OH:22])([CH3:10])([CH3:9])[CH3:8]

Participants

9

Reactant 4

HCID 1049PyridineHCID 21552-AminothiazoleHCID 24489Sodium DithioniteHCID 14373787HCID 14373787, compound

Product 1

HCID 19822291HCID 19822291, compoundYield 12.4%

Reagents, catalysts & solvents 4

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (3.71 ml) was dissolved in 137 ml of dichloroethane, followed by addition of 1.26 ml of titanium tetrachloride. The mixture was heated under reflux for 15 minutes. Then, 5.00 g of 2-tert-butyl-5,6,7,8-tetrahydro-1,4-naphthoquinone and 2.29 g of 2-aminothiazole were added, and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled to room temperature and filtered through Celite pad. The insoluble matter was washed with ethyl acetate. The filtrate was concentrated, and the crude product thus obtained was dissolved in 49 ml of tetrahydrofuran. To the solution was added a solution of 38.9 g of sodium hydrosulfite in 145 ml of water, and the mixture was stirred at room temperature for 15 minutes and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The thus-obtained crude product was purified by silica gel column chromatography (diethyl ether-hexane =2:3) and washed with isopropyl ether to give 0.86 g of the desired compound as a colorless solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2 hours
  5. filtrationfiltered through Celite pad
  6. washThe insoluble matter was washed with ethyl acetate
  7. concentrationThe filtrate was concentrated
  8. customthe crude product thus obtained
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated aqueous sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated
  13. customThe thus-obtained crude product
  14. customwas purified by silica gel column chromatography (diethyl ether-hexane =2:3)
  15. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-dbb3a8a0e2764037b5c5d1a18ba91f50
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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