Hydrochloric Acid → methyl 2-(3,4-bis(difluoromethoxy)-phenyl)-2-hydroxyacetimidate HCl salt
Reaction equation
[F:1][CH:2]([F:18])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([OH:17])[C:15]#[N:16])[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].[CH3:19][OH:20].[ClH:21]>C(Cl)Cl.O1CCOCC1>[ClH:21].[F:1][CH:2]([F:18])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([OH:17])[C:15](=[NH:16])[O:20][CH3:19])[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:12])[F:13]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To 132B (308 mg, 1.16 mmol) in anhydrous CH2Cl2 (5 mL) at 0° C. was added MeOH (0.3 mL) and 4.0 N HCl in dioxane (1.2 mL). The mixture was stirred at 0° C. for 30 min and then at rt for 4.0 h. The solvent was removed to give methyl 2-(3,4-bis(difluoromethoxy)-phenyl)-2-hydroxyacetimidate HCl salt. To this salt in CH2Cl2 (5.0 mL) was added H2O (5.0 mL). The mixture was stirred at rt for 30 min, then extracted with CH2Cl2 (2×50 mL). The combined organic extracts were dried and concentrated. The crude product was purified by silica gel chromatography to give 132C (160 mg, 46% yield) as a viscous oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.70 (s, 3H) 5.23 (s, 1H) 6.81 (t, J=73.60 Hz, 2H) 7.26-7.38 (m, 2H) 7.40 (s, 1H).
Workup
- waitat rt for 4.0 h
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-c410345819b249aab92135577151333c
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622585B2
Reaction notes
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