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

HRID 1398856ノート

反応式

HRID 1398856 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-9e1d23fce31648f2a9f14daf9138385e
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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