Thionyl Chloride → 4-Chloro-6-iodoquinazoline

HRID 871386Notes

Reaction equation

HRID 871386 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.O=S(Cl)[Cl:15]>CN(C=O)C>[Cl:15][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354016666-Iodoquinazolin-4-one

Product 1

HCID 111738094-Chloro-6-iodoquinazolineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
90 °C

Procedure

To a mixture of 6-iodoquinazolin-4(3H)-one (1.70 g, 6.25 mmol) in SOCl2 (10 mL) was dropped a few drops of DMF, and then it was heated at 90° C. for 5 hours. After excess SOCl2 was removed under reduced pressure, to it was added CH2Cl2 and water, and neutralized with saturated NaHCO3 solution. The aqueous was extracted with CH2Cl2 three times. Extracts were dried over MgSO4 and concentrated under reduced pressure to afford 4-chloro-6-iodoquinazoline as solid (1.266 g, 70%). 1H NMR (300 MHz, CDCl3) δ 9.07 (s, 1H), 8.67 (d, 1H), 8.22 (dd, 1H), 7.81 (d, 1H).

Workup

  1. customAfter excess SOCl2 was removed under reduced pressure, to it
  2. additionwas added CH2Cl2 and water
  3. extractionThe aqueous was extracted with CH2Cl2 three times
  4. dry with materialExtracts were dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04e4eb896b264fb2853225393ff0df73
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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