Thiomorpholine → (3-Nitro-5-(trifluoromethyl)phenyl)(thiomorpholino)-methanone
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[NH:26]1[CH2:31][CH2:30][S:29][CH2:28][CH2:27]1>S(Cl)(Cl)=O.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]([N:26]2[CH2:31][CH2:30][S:29][CH2:28][CH2:27]2)=[O:9])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)([O-:3])=[O:2]Participants
6
Procedure
3-Nitro-5-(trifluoromethyl)benzoic acid (2.96 g, 12.6 mmol) was allowed to reflux in thionyl chloride (6 mL) for 6 h. The resulting solution was allowed to cool to room temperature and then concentrated under reduced pressure. The resulting solid was taken up in CH2Cl2 (20 mL) and iPr2NEt (2.6 mL, 15.1 mmol) and thiomorpholine (1.4 mL, 13.8 mmol) was added. The reaction was stirred at RT for 1 h and then diluted with CH2Cl2 (50 mL). The organic layer was washed with aq. HCl (1 M, 25 mL), 9% aq. Na2CO3 (25 mL)), brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford (3-nitro-5-(trifluoromethyl)phenyl)(thiomorpholino)-methanone.
Workup
- concentrationconcentrated under reduced pressure
- washThe organic layer was washed with aq. HCl (1 M, 25 mL), 9% aq. Na2CO3 (25 mL)), brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-33b9391d12724acf8d932a0217e845d2
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07880000B2
Reaction notes
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