Phosphorus oxychloride → 4-Chloro-6,7-diethoxyquinazoline

HRID 871264Notes

Reaction equation

HRID 871264 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH3:16])[N:10]=[CH:9][NH:8][C:7]2=O)[CH3:2].O=P(Cl)(Cl)[Cl:20]>C1(C)C=CC=CC=1>[Cl:20][C:7]1[C:6]2[C:11](=[CH:12][C:13]([O:14][CH2:15][CH3:16])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[N:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354614006,7-diethoxyquinazolin-4(3H)-one

Product 1

HCID 116874744-Chloro-6,7-diethoxyquinazolineYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

According to the procedure described in Example 6A Step 5, a mixture of 6,7-diethoxyquinazolin-4(3H)-one (1.70 g, 7.3 mmol) and POCl3 (3 mL) in toluene (10 mL) was heated at 120° C. for 5 hours to afford 4-chloro-6,7-diethoxyquinazoline as a solid (1.794 g, 98%). 1H NMR (300 MHz, CDCl3) δ 8.88 (s, 1H), 7.45 (s, 1H), 7.39 (s, 1H), 4.31 (m, 4H), 1.58 (m, 6H); LC-MS (ESI) m/z 253 (M+H)+.

Sources & evidence

ORD record
ord-dff2087573d0499c97ba5fb2deb5cfe6
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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