Ethanol → HCID 16064531, compound
Reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)[NH2:2].C(O)C.[F:16][C:17]([F:31])([F:30])[C:18](=O)[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)=O>>[CH3:28][C:25]1[CH:24]=[CH:23][C:22]([C:20]2[N:1]([C:3]3[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:10])=[O:11])=[CH:5][CH:4]=3)[N:2]=[C:18]([C:17]([F:16])([F:30])[F:31])[CH:19]=2)=[CH:27][CH:26]=1Participants
4
Procedure
To a stirred suspension of p-hydrazino-benzenesulfonic acid (42 g, 0.223 mol) in ethanol (450 ml) 6N hydrochloric acid (74 ml, 0.446 mol) was added at room temperature, followed by addition of 4,4,4-trifluoro-1-(4-methyl-phenyl)-butane-1,3-dione (51.45 g, 0.223 mol). The obtained suspension was refluxed for 8 h, then concentrated in vacuo. The residue was dissolved in water (300 ml) and extracted with ethyl acetate (2×200 ml). The combined organic layers were washed with water (1×100 ml) and brine (1×100 ml), dried over MgSO4, decolorized, filtered and concentrated in vacuo. The obtained crystalline product was recrystallized from diisopropyl ether (300 ml) to yield 70.12 g (82%) of the title compound.
Workup
- additionwas added at room temperature
- temperatureThe obtained suspension was refluxed for 8 h
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in water (300 ml)
- extractionextracted with ethyl acetate (2×200 ml)
- washThe combined organic layers were washed with water (1×100 ml) and brine (1×100 ml)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe obtained crystalline product was recrystallized from diisopropyl ether (300 ml)
Sources & evidence
- ORD record
- ord-8309d7b80b2e41118eb084bf235fbb9a
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723370B2
Reaction notes
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