Hydrochloric Acid → HCID 59202375, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH:19][C:20](=[O:33])[C:21]1[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[CH:23][C:22]=1[NH:30][CH2:31][CH3:32].[Sn](Cl)(Cl)(Cl)Cl.Cl>C(O)(C)C>[NH2:27][C:25]1[CH:24]=[CH:23][C:22]([NH:30][CH2:31][CH3:32])=[C:21]([CH:26]=1)[C:20]([NH:19][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([C:8]([F:17])([C:13]([F:14])([F:15])[F:16])[C:9]([F:11])([F:12])[F:10])=[CH:5][C:4]=1[CH3:18])=[O:33]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-ethylamino-5-nitrobenzamide (3.0 g, 6.2 mmol) (see Example I5) was dissolved in isopropanol (50 ml) and tin chloride (4.2 g, 22.3 mmol) was added. The mixture was cooled to 0° C. and a solution of concentrated hydrogen chloride (6 ml) was added slowly. The reaction mixture was stirred at 80° C. for 2 hours. Then ⅓ of the total volume of isopropanol was evaporated. Water (100 ml) was added to the concentrated mixture and a solution of aqueous sodium hydroxide (4N) to adjust the pH to 7-8. The aqueous phase was extracted three times with ethyl acetate (200 ml). The combined organic extracts were dried over sodium sulfate and concentrated. The residue was used without further purification (2.8 g, 100% yield).
Workup
- customThen ⅓ of the total volume of isopropanol was evaporated
- additionWater (100 ml) was added to the concentrated mixture
- extractionThe aqueous phase was extracted three times with ethyl acetate (200 ml)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- concentrationconcentrated
- customThe residue was used without further purification (2.8 g, 100% yield)
Sources & evidence
- ORD record
- ord-da270ef212524a14931110d54f357ea7
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420855B2
Reaction notes
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