Thionyl Chloride → 4,6-Dichloro-8-iodoquinazoline

HRID 1049936Notes

Reaction equation

HRID 1049936 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([I:12])[CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.S(Cl)([Cl:16])=O>CN(C=O)C>[Cl:16][C:5]1[C:4]2[C:9](=[C:10]([I:12])[CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1363443786-Chloro-8-iodo-4(3H)-quinazolinone

Product 1

HCID 867039334,6-Dichloro-8-iodoquinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To around bottom flask was added 6-chloro-8-iodo-3H-quinazolin-4-one (1000 mg, 3.3 mmol); and thionyl chloride (50 mL). DMF (0.1 mL) was then added, and the reaction was stirred at reflux for 2 h. The reaction was cooled to room temperature, then concentrated via rotovap. The product was then azeotroped 2× with DCM, then dried under vacuum yielding 4,6-dichloro-8-iodo-quinazoline, carried immediately to the next step. 1H NMR (400 MHz, DMSO) δ 9.24-9.20 (s, 1H), 8.77-8.73 (d, J=2.2 Hz, 1H), 8.36-8.31 (d, J=2.2 Hz, 1H).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated via rotovap
  3. customThe product was then azeotroped 2× with DCM
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b5cc936f12de42bd83ce573c6b6ca03d
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

Loading…