2,6-Di-t-butyl-p-benzoquinone → HCID 13922094, compound

HRID 1030227Notes

Reaction equation

HRID 1030227 reaction equation
[C:1]([C:5]1[C:6](=[O:16])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:9](=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[S:19][C:20]([CH3:23])=[CH:21][N:22]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>ClC(Cl)C.O.[Cl-].[Ti](Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]([NH:17][C:18]2[S:19][C:20]([CH3:23])=[CH:21][N:22]=2)[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 128672,6-Di-t-butyl-p-benzoquinoneHCID 24489Sodium DithioniteHCID 3517702-Amino-5-methylthiazole

Product 1

HCID 13922094HCID 13922094, compoundYield 33.6%

Reagents, catalysts & solvents 3

HCID 131717292HCID 131717292, compoundCatalystHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

2,6-Di-tert-butyl-1,4-benzoquinone (2.20 g) and 3.43 g of 2-amino-5-methylthiazole were dissolved in 60 ml of anhydrous dichloroethane, 0.55 ml of titanium tetrachloride chloride was added, and the mixture was heated under reflux for 14.5 hours. The mixture was then cooled to room temperature, a solution of 40 g of sodium hydrosulfite in 150 ml of water was added, and the resultant mixture was stirred for 2 hours. The insoluble matter was filtered off, the filtrate was allowed to undergo phase separation, and the aqueous layer was further extracted with dichloromethane. The organic layers were combined, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated. Purification of the crude product thus obtained by silica gel column chromatography (diethyl ether-hexane =3:7) gave 1.07 g of the desired compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14.5 hours
  3. filtrationThe insoluble matter was filtered off
  4. customphase separation
  5. extractionthe aqueous layer was further extracted with dichloromethane
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification of the crude product
  10. customthus obtained by silica gel column chromatography (diethyl ether-hexane =3:7)

Sources & evidence

ORD record
ord-8ad7d0089d38400f89a060a5056d7b99
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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