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

HRID 1628503노트

반응식

HRID 1628503 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 27360131,5-Dichloro-2-isothiocyanato-3-methylbenzene수율 58%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-08d23939953b4891af48b607a722e0b9
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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