Methanimidamide, hydrochloride (1:1) → 6,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-one

HRID 1917656Notes

Reaction equation

HRID 1917656 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][O:16][CH3:17])[C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:9][C:3]=1[C:4](OCC)=[O:5].Cl.[CH:24](N)=[NH:25]>C(N)=O>[CH3:22][O:21][CH2:20][CH2:19][O:18][C:10]1[CH:9]=[C:3]2[C:2](=[CH:12][C:11]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:1]=[CH:24][NH:25][C:4]2=[O:5]

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 11347513Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate

Product 1

HCID 1354093056,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-oneYield 56%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Conditions

Temperature
130 °C

Procedure

According to the procedure described in Example 6A Step 4, a mixture of ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate (7.15 g, 22.8 mmol) and formamidine hydrochloride (2.012 g, 25 mmol) in formamide (20 mL) was heated at 130° C. for 12 hours, to afford 6,7-bis(2-methoxyethoxy)quinazolin-4(3H)-one as a solid (3.75 g, 56%). 1H NMR (300 MHz, CDCl3) δ 10.89 (br, 1H), 8.00 (s, 1H), 7.62 (s, 1H), 7.16 (s, 1H), 4.29 (t, 4H), 3.86 (t, 4H), 3.48 (s, 6H); LC-MS (ESI) m/z 295 (M+H)+.

Sources & evidence

ORD record
ord-6519485ef3f540f788226dbd473bbc60
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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