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Pyridazine → 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridazinyl]-2H-1,4-thiazin-3(4H)-one

HRID 2292004
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HRID 2292004 반응식
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH3:16][C:17]1[NH:18][C:19](=[O:23])[CH2:20][S:21][CH:22]=1>C(#N)C>[CH3:16][C:17]1[NH:18][C:19](=[O:23])[CH2:20][S:21][C:22]=1[CH:14]1[CH:13]=[CH:12][N:11]([C:5]([O:4][CH2:3][C:2]([Cl:9])([Cl:8])[Cl:1])=[O:6])[N:10]=[CH:15]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 9259PyridazineHCID 870632,2,2-Trichloroethyl chloroformateHCID 2900175-Methyl-2h-1,4-thiazin-3(4h)-one

생성물 1

HCID 136724185-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridazinyl]-2H-1,4-thiazin-3(4H)-one수율 63%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2,2,2-Trichloroethylchloroformate (3.44 ml) was added dropwise to a solution of pyridazine (1.44 ml) in dry acetonitrile (40 ml) under ice-cooling, and the mixture was stirred for 10 minutes. 5-Methyl-2H-1,4-thiazin-3(4H)-one (1.29 g) was added to the mixture. The reaction mixture was further stirred at ambient temperature for 1 hour. Then, the solvent was removed under reduced pressure and the residue was extracted with chloroform. The extract was washed with 2N hydrochloric acid and successively with water, was dried over mangnesium sulfate and the solvent was removed. The residue was chromatographed on silica gel (Wakogel C-200) column, using ethyl acetate-n-hexane (=1:1) as an eluant to give the titled compound (2.4 g, yield 63%) as white crystals.

후처리

  1. temperaturecooling
  2. stirringThe reaction mixture was further stirred at ambient temperature for 1 hour
  3. customThen, the solvent was removed under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washThe extract was washed with 2N hydrochloric acid and successively with water
  6. dry with materialwas dried over mangnesium sulfate
  7. customthe solvent was removed
  8. customThe residue was chromatographed on silica gel (Wakogel C-200) column

출처 및 근거

ORD 기록
ord-7167639674b24dadb6e45c97c46270d7
출처 데이터셋
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04800201

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