Phosphorus oxychloride → 4-Chloro-8-iodo-2,7-dimethylquinazoline

HRID 2092299Notes

Reaction equation

HRID 2092299 reaction equation
[I:1][C:2]1[C:3]([CH3:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[NH:8][C:7]2=O.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:7]1[C:6]2[C:11](=[C:2]([I:1])[C:3]([CH3:14])=[CH:4][CH:5]=2)[N:10]=[C:9]([CH3:12])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1359656988-Iodo-2,7-dimethylquinazolin-4(3H)-one

Product 1

HCID 584664654-Chloro-8-iodo-2,7-dimethylquinazolineYield 94.2%

Conditions

Temperature
120 °C

Procedure

8-Iodo-2,7-dimethylquinazolin-4(3H)-one (0.300 g, 1.00 mmol) was treated with phosphorus oxychloride (10 mL, 107 mmol) and the mixture stirred at 120° C. for 4 h. During this time, the reaction went from being a milky white suspension to a clear solution. The mixture was concentrated under vacuum and the residual phosphorous oxychloride was azeotroped with toluene. The residue was taken up in DCM and washed with cold water (2×) followed by washes (2×) with aqueous saturated sodium bicarbonate and brine. The organic solution was then dried with sodium sulfate and concentrated under vacuum to give 4-chloro-8-iodo-2,7-dimethylquinazoline (0.30 g, 94%) as an orange solid. MS (M+H)+ 319.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residual phosphorous oxychloride was azeotroped with toluene
  3. washwashed with cold water (2×)
  4. dry with materialThe organic solution was then dried with sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-69c6e067f3774f57bdc5b76b35bce079
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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