Toluene → 4,6-Dichloro-2-methylquinazoline

HRID 1391909Notes

Reaction equation

HRID 1391909 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]=[C:5]2O.P(Cl)(Cl)([Cl:16])=O.C(N(CC)CC)C.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:16][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[C:7]([CH3:12])[N:6]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178433409HCID 178433409, compound

Product 1

HCID 210882724,6-Dichloro-2-methylquinazolineYield 48.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-2-methyl-quinazolin-4-ol (0.75 g, 3.90 mmol, 1 eq.), phosphorous oxychloride (3.47 mL, 37.4 mmol, 9.64 eq.) and triethylamine (1.62 mL, 12.5 mmol, 3.21 eq.) were refluxed for 4 hours. The mixture was stripped twice from toluene and the residue dissolved in ethyl acetate. The organic layer was washed with saturated NH4Cl (2×), dried and stripped. The residue was flash chromatographed in 3:2 ethyl acetate/hexanes to yield 400 mg of a light yellow solid product. MS (ES+)=213/215/217 (M+H)++.

Workup

  1. washThe organic layer was washed with saturated NH4Cl (2×)
  2. customdried
  3. customchromatographed in 3:2 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-aef025384c514e45b670b8dfc0aaeedf
Source dataset
uspto-grants-2008_03
Patent number
US07338947B2

Reaction notes

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