Dimethylformamide → 4-Chloro-2-(thiophen-2-yl)quinazoline

HRID 1973876Notes

Reaction equation

HRID 1973876 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:15][C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.CN(C)C=O.S(Cl)([Cl:24])=O>>[Cl:24][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[N:15]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354154992-(2-Thienyl)-4(3H)-quinazolinone

Product 1

HCID 20909944-Chloro-2-(thiophen-2-yl)quinazoline

Procedure

To a stirred suspension of 22.8 g of 2-(2-thienyl)-quinazolin-4(3H)-one in 200 ml of thionyl chloride was added in small quantities 7.3 g of dimethylformamide. The mixture was stirred for 2 hours, then poured into 2 liters of ice. The yellow solid was recrystallized three times from cyclohexane to give 16.7 g of 4-chloro-2-(2-thienyl)-quinazoline, m.p. 121.5°-123°; ir and nmr spectra were consistent with the assigned structure.

Workup

  1. customThe yellow solid was recrystallized three times from cyclohexane

Sources & evidence

ORD record
ord-c2320904830148d48e4330644e192a37
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

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