Hydrochloric Acid → 4-Chloro-2-fluoro-3-methoxybenzamidine hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[C:3]=1[O:11][CH3:12].C[Si]([N-:17][Si](C)(C)C)(C)C.[Li+].CC(O)C.Cl>C1COCC1.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:17])=[NH:7])=[C:4]([F:10])[C:3]=1[O:11][CH3:12]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
4-chloro-2-fluoro-3-methoxybenzonitrile (3.0 g, 16 mmol) was dissolved in 7 mL dry THF and added dropwise to a 1M solution of lithium bis(trimethylsilyl)amide (18 mL, 18 mmol). After stirring at 25° C. for 5 h, the mixture was treated with 25 mL of 2-propanol saturated with gaseous HCl. Upon standing at 5° C. for 18 h, the mixture was diluted with 30 mL ether whereupon the product precipitated. The precipitated product was collected by filtration, washed with ether and dried under vacuum to give the title compound (3.0 g, 78.6% yield): 1H NMR (DMSO-d6) δ 9.70 (br d, 3H), 7.58 (m, 1H), 7.46 (m, 1H), 7.39 (br d, 1H), 3.96 (s, 3H).
Workup
- waitUpon standing at 5° C. for 18 h
- customprecipitated
- filtrationThe precipitated product was collected by filtration
- washwashed with ether
- customdried under vacuum
Sources & evidence
- ORD record
- ord-fe22bd99c3f949f497aab6a7f87bc449
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609592B2
Reaction notes
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