Pyridine → HCID 67898895, compound

HRID 1030231Notes

Reaction equation

HRID 1030231 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[C:9](=O)[CH:10]=[C:11]([CH3:16])[C:12](=[O:15])[C:13]=1[CH3:14].[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1>ClC(Cl)C.[Ti](Cl)(Cl)(Cl)Cl>[S:20]1[CH:21]=[CH:22][N:23]=[C:19]1[N:18]=[C:9]1[CH:10]=[C:11]([CH3:16])[C:12]([OH:15])=[C:13]([CH3:14])[CH:8]1[CH3:7]

Participants

6

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

Product 1

HCID 67898895HCID 67898895, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

Pyridine (3.24 ml) was dissolved in 120 ml of dichloroethane, followed by addition of 1.10 ml of titanium tetrachloride. The mixture was heated under reflux for 15 minutes. Then, 3.00 g of 2,3,5-trimethyl-1,4-benzoquinone and 2.00 g of 2-aminothiazole were added, and the resultant mixture was heated under reflux for 2 hours. The reaction mixture was cooled to room temperature and filtered through a Celite pad, and the insoluble matter was washed with chloroform. The filtrate was concentrated, and the crude product obtained was purified by silica gel column chromatography (diethyl ether-hexane =1:19 1:4) to give 0.70 g of 4-(2-thiazolylimino)-2,3,6-trimethylphenol as a pale red solid melting at 95°-96° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 minutes
  3. temperatureunder reflux for 2 hours
  4. filtrationfiltered through a Celite pad
  5. washthe insoluble matter was washed with chloroform
  6. concentrationThe filtrate was concentrated
  7. customthe crude product obtained
  8. customwas purified by silica gel column chromatography (diethyl ether-hexane =1:19 1:4)

Sources & evidence

ORD record
ord-17327280f00643c1b16314bdd60b518a
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

Loading…