Methanimidamide, hydrochloride (1:1) → 7,8-dihydro-[1,4]dioxino[2,3-g]quinazolin-4(3H)-one

HRID 631225Notes

Reaction equation

HRID 631225 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([O:14]CC)=O)=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.Cl.[CH:18](N)=[NH:19]>C(N)=O>[N:1]1[C:2]2[C:3](=[CH:4][C:5]3[O:10][CH2:9][CH2:8][O:7][C:6]=3[CH:11]=2)[C:12](=[O:14])[NH:19][CH:18]=1

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 19589924HCID 19589924, compound

Product 1

HCID 1357365997,8-dihydro-[1,4]dioxino[2,3-g]quinazolin-4(3H)-oneYield 84%

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 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate (1.45 g, 6.5 mmol) and formamidine hydrochloride (1.208 g, 15 mmol) in formamide (20 mL) was heated at 130° C. for 8 hours, to afford 7,8-dihydro-[1,4]dioxino[2,3-g]quinazolin-4(3H)-one as a solid (1.114 g, 84%). 1H NMR (300 MHz, CDCl3 and drops DMSO-d6) δ 11.80 (br, 1H), 7.88 (s, 1H), 7.63 (s, 1H), 7.13 (s, 1H), 4.36 (m, 4H); LC-MS (ESI) m/z 205 (M+H)+.

Sources & evidence

ORD record
ord-0fef58edf58f47048bc537d94e6ab547
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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