4-Chloro-6-iodoquinazoline Chemical Properties

Melting point:

175.0 to 179.0 °C

Boiling point:

363.2±22.0 °C(Predicted)

Density 

2.017±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

pka

0.15±0.30(Predicted)

form 

Solid

color 

Light Brown to Dark Grey

Stability:

Hygroscopic

InChI

InChI=1S/C8H4ClIN2/c9-8-6-3-5(10)1-2-7(6)11-4-12-8/h1-4H

InChIKey

BDAIUOPDSRAOKI-UHFFFAOYSA-N

SMILES

N1=C2C(C=C(I)C=C2)=C(Cl)N=C1

CAS DataBase Reference

98556-31-1(CAS DataBase Reference)

Safety Information

HS Code 

2933599590

4-Chloro-6-iodoquinazoline Usage And Synthesis

Chemical Properties

Dark Grey Solid

Uses

4-Chloro-6-iodoquinazoline is an intermediate in the synthesis of Lapatinib (L175800).

Synthesis

Step B: Synthesis of 4-chloro-6-iodoquinazoline. Anhydrous dimethylformamide (DMF, 3.20 ml) was added to a stirred solution of 1,2-dichloroethane (DCE, 10 ml) under nitrogen protection and subsequently cooled in an ice water bath. A solution of oxalyl chloride (5.2 ml, 60 mmol) in DCE (25 ml) was slowly added dropwise. Formation of white precipitate was observed during dropwise addition. After completion of dropwise addition, the ice water bath was removed and the reaction mixture was continued to be stirred at room temperature for 5 minutes. Under nitrogen atmosphere, 6-iodo-4(H)-quinazolinone (5.0 g, 18 mmol) was added in batches, followed immediately by heating the mixture to reflux. After maintaining the reflux reaction for 4.5 h, it was cooled to room temperature. The reaction mixture was poured into an excess of ice-water mixture (about 300 ml) and extracted with dichloromethane (DCM, about 500 ml). The aqueous layer was further extracted with DCM (2 x 50 ml). All organic extracts were combined, dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give 5.2 g (99% yield) of 4-chloro-6-iodoquinazoline as a brown solid.

References

[1] Patent: US2005/101617, 2005, A1. Location in patent: Page/Page column 6
[2] Patent: WO2011/2523, 2011, A1. Location in patent: Page/Page column 43
[3] Patent: KR2017/15848, 2017, A. Location in patent: Paragraph 0067; 0071; 0072
[4] Patent: CN106317026, 2017, A. Location in patent: Paragraph 0075; 0076; 0077; 0078
[5] Patent: CN103772411, 2016, B. Location in patent: Paragraph 0017; 0027; 0028

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