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

HRID 1176037Notes

Reaction equation

HRID 1176037 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) 7.82 (d, 1H), 8.45 (d, 1H), 8.63 (s, 1H).

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-0e4a6b4f069a4b27828d7b47ef73da12
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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