Ethyl Acetate → HCID 72312772, compound

HRID 1161498Notes

Reaction equation

HRID 1161498 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10].[CH3:14][O:15][C:16](=[O:45])[N:17]=[C:18]([S:43][CH3:44])[C:19]([C:33]1[CH:38]=[C:37]([CH2:39][CH3:40])[CH:36]=[C:35]([OH:41])[C:34]=1[F:42])=[N:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)=[CH:23][CH:22]=1.C(OCC)(=O)C>CN(C=O)C.O>[CH3:14][O:15][C:16](=[O:45])[N:17]=[C:18]([S:43][CH3:44])[C:19]([C:33]1[CH:38]=[C:37]([CH2:39][CH3:40])[CH:36]=[C:35]([O:41][CH2:8][C:9](=[O:10])[N:11]([CH3:13])[CH3:12])[C:34]=1[F:42])=[N:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 72312790HCID 72312790, compound

Product 1

HCID 72312772HCID 72312772, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

After adding 0.163 g of potassium carbonate and 0.14 ml of 2-chloro-N,N-dimethylacetamide to a solution of 0.41 g of {2-(5-ethyl-2-fluoro-3-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 15 ml of DMF, the reaction mixture was stirred at room temperature for 60 hours, and then 200 ml of ethyl acetate and 100 ml of water were added. The organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order, and dried over anhydrous magnesium sulfate. The desiccating agent was filtered, 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 (0.41 g) as a light yellow solid.

Workup

  1. washThe organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered
  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-1c83ae186b4d448f845635c17c48c87d
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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