Methanimidamide, hydrochloride (1:1) → 6,7-diethoxyquinazolin-4(3H)-one

HRID 631218Notes

Reaction equation

HRID 631218 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:10]([O:16][CH2:17][CH3:18])=[CH:9][C:3]=1[C:4](OCC)=[O:5].Cl.[CH:20](N)=[NH:21]>C(N)=O>[CH2:17]([O:16][C:10]1[CH:9]=[C:3]2[C:2](=[CH:12][C:11]=1[O:13][CH2:14][CH3:15])[N:1]=[CH:20][NH:21][C:4]2=[O:5])[CH3:18]

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 11807180Ethyl 2-amino-4,5-diethoxybenzoate

Product 1

HCID 1354614006,7-diethoxyquinazolin-4(3H)-oneYield 73%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Conditions

Temperature
140 °C

Procedure

According to the procedure described in Example 6A Step 4, a mixture of ethyl 2-amino-4,5-diethoxybenzoate (2.53 g, 10 mmol) and formamidine hydrochloride (0.966 g, 12 mmol) in formamide (10 mL) was heated at 140° C. for 5 hours, to afford 6,7-diethoxyquinazolin-4(3H)-one as a white solid (1.702 g, 73%). 1H NMR (300 MHz, CDCl3) δ 10.49 (br, 1H), 7.98 (s, 1H), 7.60 (s, 1H), 7.14 (s, 1H), 4.24 (m, 4H), 1.54 (m, 6H); LC-MS (ESI) m/z 235 (M+H)+.

Sources & evidence

ORD record
ord-f276ab36c67b4a85889695156f93d449
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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