Water → HCID 22024640, compound

HRID 501004Notes

Reaction equation

HRID 501004 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(C(C)C)C(C)C)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][N:28]=[N:27][C:26]=2[N:31]=[C:32](SC)[S:33][CH3:34])=[C:21]([CH3:37])[CH:20]=1.O>C(#N)C>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:26]3[N:27]([C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:32]([S:33][CH3:34])[N:31]=3)[N:28]=[CH:29][CH:30]=2)=[C:21]([CH3:37])[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 22024389HCID 22024389, compound

Product 1

HCID 22024640HCID 22024640, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl bromoacetate (0.87 mL) and i-Pr2EtN (1.36 mL) were added to a solution of methyl N-[4-(4-methoxy-2-methylphenyl)-3-pyridazinyl]-(methylsulfanyl)methaneimidothioate (1.25 g) in acetonitrile (10 mL), and the mixture was heated under stirring at 100° C. for 14 hours. The reaction mixture was cooled to room temperature, which was added with water, extracted with ethyl acetate, and washed with water. After that, it was dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (628 mg) as a red brown oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialAfter that, it was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-be94f30c3afd49ac856fc4fa269e0521
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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