Water → S-4-benzyl-2-nitrophenyl dimethylcarbamothioate

HRID 2075252ノート

反応式

HRID 2075252 の反応式
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11](O)=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20][N:21]([CH3:25])[C:22](Cl)=[S:23].[OH2:26]>CN(C=O)C>[CH3:20][N:21]([CH3:25])[C:22](=[O:26])[S:23][C:11]1[CH:12]=[CH:13][C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 7863744-Benzyl-2-nitrophenol

生成物 1

HCID 58415382S-4-benzyl-2-nitrophenyl dimethylcarbamothioate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a yellow solution of 4-benzyl-2-nitrophenol (2.0 g, 8.7 mmol) in 20 mL DMF at 0° C. was added sodium hydride (0.38 g, 9.6 mmol). The reaction became deep orange, and after 30 min dimethylthiocarbamoyl chloride (1.2 g, 9.6 mmol) was added. The reaction was stirred over the weekend at room temperature. Water was added, and the mixture was extracted with DCM 3 times. The combined extracts were washed with 0.5M NaHCO3, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. The oil was heated to 160° C. for a total of 2 h. The reaction was cooled, and the resulting oil was loaded directly onto a 120 g ISCO column and eluted with 0-30-50% EtOAc/hexanes, to give S-4-benzyl-2-nitrophenyl dimethylcarbamothioate. MS (ESI) m/z: Calculated: 316.1; Observed: 317.1 (M++1).

後処理

  1. extractionthe mixture was extracted with DCM 3 times
  2. washThe combined extracts were washed with 0.5M NaHCO3
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. temperatureThe oil was heated to 160° C. for a total of 2 h
  8. temperatureThe reaction was cooled
  9. washeluted with 0-30-50% EtOAc/hexanes

出典と根拠

ORDレコード
ord-1f4cc8af0ed14eaeb808e03e1bc7e0bb
出典データセット
uspto-grants-2011_04
特許番号
US07919519B2

反応ノート

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