Phosphorus oxychloride → 4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline

HRID 1917657Notes

Reaction equation

HRID 1917657 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][NH:10][C:9]2=O.O=P(Cl)(Cl)[Cl:24]>C1(C)C=CC=CC=1>[Cl:24][C:9]1[C:8]2[C:13](=[CH:14][C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354093056,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-one

Product 1

HCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazolineYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

According to the procedure described in Example 6A Step 5, a mixture of 6,7-bis(2-methoxyethoxy)quinazolin-4(3H)-one (2.28 g, 7.7 mmol) and POCl3 (10 mL) in toluene (30 mL) was heated at 125° C. for 5 hours, to afford 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline as a solid (2.212 g, 91%). 1H NMR (300 MHz, CDCl3) δ 8.86 (s, 1H), 7.44 (s, 1H), 7.34 (s, 1H), 4.34 (t, 4H), 3.89 (t, 4H), 3.50 (s, 3H), 3.49 (s, 3H); LC-MS (ESI) m/z 313 (M+H)+.

Sources & evidence

ORD record
ord-21a4f73e2b2e4d8aa03e91347d6bacfb
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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