Thionyl Chloride → 4-Chloro-2-[4-(1,1-dimethylethyl)phenyl]quinazoline

HRID 1973875Notes

Reaction equation

HRID 1973875 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:20][C:19](=O)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:24])=O>CN(C)C=O>[Cl:24][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[N:20]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 135443955ST50050588

Product 1

HCID 7320204-Chloro-2-[4-(1,1-dimethylethyl)phenyl]quinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.9 g of 2-(4-tert-butylphenyl)quinazolin-4(3H)-one and 60 ml of thionyl chloride was treated with 2.34 g of dimethylformamide as described in Example VI. The initial solid was triturated with cyclohexane, filtered, and the filtrate concentrated to give an oil which solidified on standing to give a solid, m.p. 74°-77°. This solid was recrystallized twice from petroleum ether (30°-60° fraction) using a low-temperature recrystallization apparatus to give 6.3 g of 4-chloro-2-(4-tert-butylphenyl)quinazoline, m.p. 75°-76.5°; ir and nmr spectra were consistent with the assigned structure.

Workup

  1. customThe initial solid was triturated with cyclohexane
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated
  4. customto give an oil which
  5. customto give a solid, m.p. 74°-77°
  6. customThis solid was recrystallized twice from petroleum ether (30°-60° fraction)

Sources & evidence

ORD record
ord-3209e675730749f5afffe73be128c19e
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

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