Hydrochloric Acid → HCID 87455115, compound
Reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])[CH:6]=1)[C:3]#[N:4].CO.[ClH:20].[O:21]1CCOC[CH2:22]1>C(OCC)C>[ClH:20].[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:16])([F:17])[CH:13]([F:14])[F:15])[CH:6]=1)[C:3](=[NH:4])[O:21][CH3:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 130A (249 mg, 1.0 mmol) in anhydrous diethyl ether (4 mL) at 0° C. was added MeOH (0.4 mL, 10 mmol) and 4.0 N HCl in dioxane (2.0 mL, 8 mmol). 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-hydroxy-2-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)acetimidate HCl salt. To this salt in CH2Cl2 (4.0 mL) was added H2O (8.0 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 130B (170 mg, 60% yield) as a viscous oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.73 (s, 3H) 5.14 (s, 1H) 5.71-6.08 (m, 1H) 7.17 (d, J=7.03 Hz, 1H) 7.28 (s, 1H) 7.31-7.43 (m, 2H).
Workup
- waitat rt for 4.0 h
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-c536aad2e6da4bf8b19411a1a9f640b1
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622585B2
Reaction notes
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