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

HRID 502710ノート

反応式

HRID 502710 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-098305c2d9694224b9f0061ba163aa9b
出典データセット
uspto-grants-2010_08
特許番号
US07776869B2

反応ノート

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