Thiophosgene → 5-Isothiocyanato-2-methoxy-4-methylpyridine

HRID 1398857

반응식

HRID 1398857 반응식
[C:1](Cl)(Cl)=[S:2].[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:14])[CH:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:13]([C:10]1[C:9]([CH3:14])=[CH:8][C:7]([O:6][CH3:5])=[N:12][CH:11]=1)=[C:1]=[S:2]

참가 물질

5

반응물 2

HCID 10040ThiophosgeneHCID 2431706-Methoxy-4-methylpyridin-3-amine

생성물 1

HCID 866328845-Isothiocyanato-2-methoxy-4-methylpyridine수율 59%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매2회

반응 조건

온도
0 °C

실험 절차

Thiophosgene (8.9 mL, 120 mmol) was added dropwise to a stirred mixture of 6-methoxy-4-methylpyridin-3-amine (13.8 g, 99.8 mmol) in tetrahydrofuran (100 mL) and saturated aqueous sodium hydrogen carbonate (150 mL) at 0° C., and the mixture was stirred at 0° C. for 2 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 washed with n-hexane to give the title compound as a colorless powder (10.6 g, 58.8 mmol, 59%).

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-d17bc03c4b95426fba488b1b021ca0ff
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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