Triethylamine hydrochloride → 2,4-Dichloro-6-iodoquinazoline

HRID 855652Notes

Reaction equation

HRID 855652 reaction equation
[Na].[I:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8](O)[N:7]=[C:6]2O.[ClH:15].C(N(CC)CC)C.P(Cl)(Cl)([Cl:25])=O>>[Cl:15][C:8]1[N:7]=[C:6]([Cl:25])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([I:2])[CH:4]=2)[N:9]=1

Participants

4

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 24813Phosphorus oxychlorideHCID 178518391HCID 178518391, compound

Product 1

HCID 114615062,4-Dichloro-6-iodoquinazolineYield 90%

Procedure

To a suspension of 6-iodo-quinazoline-2,4-diol sodium salt (849 mg, 2.74 mmol) in phosphorus oxychloride (20 mL), was added triethylamine hydrochloride (1.70 g, 12.32 mmol). The reaction mixture was heated at 100 C for 16 hours, then concentrated in vacuum. Ice chips were added to the remaining residue, which was diluted with dichloromethane, washed with water and saturated aqueous sodium bicarbonate, then dried over magnesium sulfate to give 2,4-dichloro-6-iodo-quinazoline as an off-white solid (799 mg, 90%). HNMR (500 MHz, DMSO) δ7.82 (d, 1H), 8.45 (d, 1H), 8.63 (s, 1H). LCMS (ES+) m/e 324.8 (M+H).

Workup

  1. temperatureThe reaction mixture was heated at 100 C for 16 hours
  2. concentrationconcentrated in vacuum
  3. additionIce chips were added to the remaining residue, which
  4. additionwas diluted with dichloromethane
  5. washwashed with water and saturated aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-3fdcdd59597444af873d914e6be8d132
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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