Dimethylformamide → 4-Chloro-6-iodoquinazoline

HRID 877077Notes

Reaction equation

HRID 877077 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2O.CN(C=O)C.S(Cl)([Cl:20])=O>>[Cl:20][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 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178518013HCID 178518013, compound

Product 1

HCID 111738094-Chloro-6-iodoquinazolineYield 99%

Procedure

To a solution of 6-Iodo-quinazolin-4-ol (5.0 g, 18 mmol) in thionyl chloride (10 mL) was added slowly DMF (0.5 mL) and the mixture is heated immediately to reflux. Heating is continued for 4.5 hours, followed by cooling to room temperature. The reaction mixture was then evaporated under reduced pressure to dryness. The residue was then redesolved in DCM (20 mL), and to it was added toluene (50 mL), and the mixture was then evaporated under reduced pressure to dryness. The procedure was repeated one more time to rid the product of thionyl chloride to yield 5.2 g (99%) of desired product as a tan solid.

Workup

  1. temperaturethe mixture is heated immediately
  2. temperatureto reflux
  3. temperatureHeating
  4. customThe reaction mixture was then evaporated under reduced pressure to dryness
  5. additionto it was added toluene (50 mL)
  6. customthe mixture was then evaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-60b959a8896a4f959c7471f6c5c95536
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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