Water → {2-[2-Fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

HRID 2079104Notes

Reaction equation

HRID 2079104 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][CH2:8][CH2:9]I.[CH3:11][O:12][C:13](=[O:42])[N:14]=[C:15]([S:40][CH3:41])[C:16]([C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([OH:38])[C:31]=1[F:39])=[N:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[C:27]([CH3:29])[O:26][N:25]=2)=[CH:20][CH:19]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:42])[N:14]=[C:15]([S:40][CH3:41])[C:16]([C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH2:9][CH2:8][F:7])[C:31]=1[F:39])=[N:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[C:27]([CH3:29])[O:26][N:25]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 72312745[2-(2-Fluoro-3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester

Product 1

HCID 72312758{2-[2-Fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterYield 97.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 3.32 g of potassium carbonate and 3.13 g of 1-fluoro-2-iodoethane to a solution of 5.5 g of [2-(2-fluoro-3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester in 100 ml of DMF, the mixture was stirred at room temperature for 15 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. After washing the organic layer with water and saturated brine, it was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (5.88 g) as a yellow solid.

Workup

  1. washAfter washing the organic layer with water and saturated brine, it
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-deb6b8a3d14b44b5803dd5a159475e7b
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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