Thiophosgene → 1,5-Dichloro-2-isothiocyanato-3-methylbenzene

HRID 1628503ノート

反応式

HRID 1628503 の反応式
[C:1](Cl)(Cl)=[S:2].[Cl:5][C:6]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([CH3:14])[C:7]=1[NH2:8]>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:5][C:6]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([CH3:14])[C:7]=1[N:8]=[C:1]=[S:2]

参加物

5

反応物 2

HCID 10040ThiophosgeneHCID 12682872,4-Dichloro-6-methylaniline

生成物 1

HCID 27360131,5-Dichloro-2-isothiocyanato-3-methylbenzene収率 58%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒2 回

実験手順

Thiophosgene (17.0 g, 148 mmol) was added dropwise to a stirred mixture of 2,4-dichloro-6-methylaniline (20.0 g, 114 mmol) in tetrahydrofuran (100 mL) and saturated aqueous sodium hydrogen carbonate (100 mL) at 0° C., and the mixture was stirred at room temperature for 90 minutes. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with n-hexane to give the title compound as a colorless powder (14.4 g, 66.0 mmol, 58%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with n-hexane

出典と根拠

ORDレコード
ord-08d23939953b4891af48b607a722e0b9
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

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