1,2-Dichloroethane → 2,6-Dichloroquinazoline

HRID 1850302Notes

Reaction equation

HRID 1850302 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](N)[N:6]=[CH:5]2.C(O[N+]([O-])=O)(C)(C)C.C([O-])(O)=O.[Na+].[Cl:26]CCCl>>[Cl:26][C:7]1[N:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 164756Nitric acid, 1,1-dimethylethyl esterHCID 516892Sodium BicarbonateHCID 211839426-Chloroquinazolin-2-amine

Product 1

HCID 124139282,6-DichloroquinazolineYield 20%

Conditions

Temperature
60 °C

Procedure

To a suspension of 6-chloro-quinazolin-2-ylamine (110) (2.8 g, 15.8 mmol) and SbCl3 (7.2 g, 32 mmol) in 1,2-dichloroethane (100 mL) was added tert-butylnitrate (6.2 ml, 52 mmol) and heated at 60° C. for 3 h under nitrogen atmosphere. To the mixture was added aqueous saturated NaHCO3 and the mixture was filtered off and filtrate was extracted with CHCl3. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by silica gel column chromatography, using CHCl3/EtOAc (9:1, v/v) as eluent to give 2,6-dichloro-quinazoline (111) (0.65 g, 3.12 mmol, 20% yield).

Workup

  1. filtrationthe mixture was filtered off
  2. extractionfiltrate was extracted with CHCl3
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-114dc365ca4b49cbb0c43ace77126036
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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