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

HRID 2292004Notes

Reaction equation

HRID 2292004 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7167639674b24dadb6e45c97c46270d7
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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