3-Chloro-benzamidine → 2-(3-Chlorophenyl)-5,6,7,8-tetrahydroquinazolin-4-ol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](=[NH:7])[NH2:6].[CH3:11][O-:12].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:6][C:11](=[O:12])[C:10]3[CH2:9][CH2:8][CH2:4][CH2:3][C:2]=3[N:7]=2)[CH:8]=[CH:9][CH:10]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A solution of 3-chlorobenzimidamide (5 g, 32.34 mmol) in ethanol (90 mL) was treated with ethyl-2-cyclohexaneonecarboxylate (6.3 g, 40.43 mmol) and sodium methoxide (2.1 g, 38.81 mmol). The reaction mixture was heated at 85° C. for 18 h. After this time, the reaction mixture was cooled and concentrated to a volume of approximately 50 mL. Then, 2.0 M HCl (68 mL) was added slowly. The resulting precipitate was filtered, washed with water and ether, and the residue was dried on a high vacuum overnight to afford the title compound (2.2 g, crude) as a light yellow solid. MW=260.72. 1H NMR (DMSO-d6, 300 MHz) δ 12.64 (s, 1H), 8.16-8.10 (m, 1H), 8.08-7.99 (m, 1H), 7.66-7.57 (m, 1H), 7.54 (t, J=7.9 Hz, 1H), 2.66-2.55 (m, 2H), 2.44-2.33 (m, 2H), 1.84-1.61 (m, 4H); APCI MS m/z 261 [M+H]+.
Workup
- temperatureAfter this time, the reaction mixture was cooled
- concentrationconcentrated to a volume of approximately 50 mL
- additionThen, 2.0 M HCl (68 mL) was added slowly
- filtrationThe resulting precipitate was filtered
- washwashed with water and ether
- customthe residue was dried on a high vacuum overnight
Sources & evidence
- ORD record
- ord-42256c5045a14738b40e43ae94177162
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221843B2
Reaction notes
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