Thionyl Chloride → HCID 821160, compound

HRID 1973874Notes

Reaction equation

HRID 1973874 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:17][C:16](=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.S(Cl)([Cl:21])=O>CN(C)C=O>[Cl:21][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 135412164HCID 135412164, compound

Product 1

HCID 821160HCID 821160, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 17.5 g of 2-(2-chlorophenyl)quinazolin-4(3H)-one and 130 ml of thionyl chloride was treated as described in Example I with 5 g of dimethylformamide. The mixture was poured into 1000 ml of ice water and stirred until the ice was melted. The solid was collected by filtration and allowed to air-dry overnight. The solid was triturated with 500 ml of boiling cyclohexane. The insoluble solid was removed by filtration and the cyclohexane solution allowed to cool slowly. The solid which separated was collected to give pale yellow needles, m.p. 127°-129°. Recrystallization of the yellow needles from cyclohexane gave 9.9 g of 4-chloro-2-(2-chlorophenyl)quinazoline, m.p. 129.5°-130.5°; ir and nmr spectra were consistent with the assigned structure.

Workup

  1. additionwas treated
  2. filtrationThe solid was collected by filtration
  3. customto air-dry overnight
  4. customThe solid was triturated with 500 ml of boiling cyclohexane
  5. customThe insoluble solid was removed by filtration
  6. temperatureto cool slowly
  7. customThe solid which separated
  8. customwas collected
  9. customto give pale yellow needles, m.p. 127°-129°
  10. customRecrystallization of the yellow needles from cyclohexane

Sources & evidence

ORD record
ord-7515a892433a46bc8ed5c7bd4026caa3
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

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