Water → 6-Chloro-3-isothiocyanato-4-methylpyridazine

HRID 1628465노트

반응식

HRID 1628465 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.[C:10](Cl)(Cl)=[S:11].O.C(OCC)(=O)C>C(=O)(O)[O-].[Na+].O1CCCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]=[C:10]=[S:11])=[C:4]([CH3:9])[CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 123536646-Chloro-4-methylpyridazin-3-amine

생성물 1

HCID 866328736-Chloro-3-isothiocyanato-4-methylpyridazine수율 8.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 6-chloro-4-methylpyridazin-3-amine (2.86 g, 20.0 mmol) in aqueous sodium bicarbonate (10 mL) and tetrahydrofuran (40 mL) was added thiophosgene (1.69 mL, 22.0 mmol) dropwise at 0° C. After stirring for 1 hr. water and ethyl acetate were added to the mixture and the insoluble materials were filtered off. The filtrate was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (304 mg, 1.64 mmol, 8%) as a pale yellow solid.

후처리

  1. filtrationthe insoluble materials were filtered off
  2. washThe filtrate was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  6. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-3710feb3e94f49b8a34380b212d05966
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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