Thiophosgene → 3,5-Dichloro-2-isothiocyanatopyridine

HRID 1398863

반응식

HRID 1398863 반응식
[C:1](Cl)(Cl)=[S:2].[Cl:5][C:6]1[C:7]([NH2:13])=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:5][C:6]1[C:7]([N:13]=[C:1]=[S:2])=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1

참가 물질

5

반응물 2

HCID 10040ThiophosgeneHCID 778863,5-Dichloro-3-pyridylamine

생성물 1

HCID 233404453,5-Dichloro-2-isothiocyanatopyridine수율 39%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매2회

실험 절차

Thiophosgene (21.9 ml, 288 mmol) was added dropwise to a stirred mixture of 3,5-dichloropyridin-2-amine (23.5 g, 144 mmol) in tetrahydrofuran (150 mL) and saturated aqueous sodium hydrogen carbonate (150 mL) at 0° C., and the mixture was stirred at room temperature for 4 hr. 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 purified by flash column chromatography on silica gel eluting with a 5-30% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (11.4 g, 55.6 mmol, 39%).

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. customThe residue was purified by flash column chromatography on silica gel eluting with a 5-30% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-baca3a2a9d6d47568444d9fe37d55cfc
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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