Thiomorpholine → (3-Nitro-5-(trifluoromethyl)phenyl)(thiomorpholino)-methanone

HRID 1042665Notes

Reaction equation

HRID 1042665 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].[NH:17]1[CH2:22][CH2:21][S:20][CH2:19][CH2:18]1>S(Cl)(Cl)=O.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]([N:17]2[CH2:22][CH2:21][S:20][CH2:19][CH2:18]2)=[O:9])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 67164ThiomorpholineHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 66970321(3-Nitro-5-(trifluoromethyl)phenyl)(thiomorpholino)-methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

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 (1M, 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

  1. concentrationconcentrated under reduced pressure
  2. washThe organic layer was washed with aq. HCl (1M, 25 mL), 9% aq. Na2CO3 (25 mL), brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d27bbecde254709bf0c688e1ce03a36
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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