Dimethylformamide → 4-Chloro-6-iodoquinazoline

HRID 1264047Notes

Reaction equation

HRID 1264047 reaction equation
CN(C=O)C.[C:6]([Cl:11])(=O)[C:7](Cl)=O.[I:12][C:13]1[CH:22]=CC2[C:15](=[CH:16][NH:17][C:18](=O)[N:19]=2)[CH:14]=1>ClCCCl>[I:12][C:13]1[CH:22]=[C:7]2[C:16](=[CH:15][CH:14]=1)[N:17]=[CH:18][N:19]=[C:6]2[Cl:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178517224HCID 178517224, compound

Product 1

HCID 111738094-Chloro-6-iodoquinazoline

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a stirred solution of DMF (6.3 mL) in DCE (20 mL) cooled to 0° C. was added dropwise a solution of oxalyl chloride (60 mL of a 2M solution in DCE). After addition was complete, the cooling bath was removed and 6-iodo-3H-quinazolinone (10 g, 36.8 mmol) was added as a solid. The resulting mixture was heated to reflux under nitrogen for 3 hours. Upon cooling to room temperature, the reaction was quenched cautiously with H20. CH2Cl2 was added and the bilayer transferred to a separatory funnel. The aqueous layer was extracted with CH2Cl2 (2×50 mL) and the combined organic layers dried (Na2SO4). The solvent was removed in vacuo to provide a yellow solid which was triturated with diethyl ether to remove any remaining impurities. The resulting yellow solid obtained by filtration was shown to be pure by NMR. 1HNMR (CDCl3, 400 MHz): δ: 9.05 (s, 1H), 8.65 (d, 1H), 8.21 (dd, 1H), 7.78 (d, 1H).

Workup

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux under nitrogen for 3 hours
  5. customthe reaction was quenched cautiously with H20
  6. additionCH2Cl2 was added
  7. customthe bilayer transferred to a separatory funnel
  8. extractionThe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  9. dry with materialthe combined organic layers dried (Na2SO4)
  10. customThe solvent was removed in vacuo
  11. customto provide a yellow solid which
  12. customwas triturated with diethyl ether
  13. customto remove any remaining impurities
  14. customThe resulting yellow solid obtained by filtration

Sources & evidence

ORD record
ord-b56074f7e1c34b35a7b7741d0622ceca
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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