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

HRID 1698731Notes

Reaction equation

HRID 1698731 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([NH:11][CH3:12])=[O:10].[CH3:13][O:14][C:15](=[O:44])[N:16]=[C:17]([S:42][CH3:43])[C:18]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([O:39][CH2:40][CH3:41])[CH:33]=1)=[N:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]=[C:29]([CH3:31])[O:28][N:27]=2)=[CH:22][CH:21]=1.O>CC(C)=O.C(OCC)(=O)C>[CH3:13][O:14][C:15](=[O:44])[N:16]=[C:17]([S:42][CH3:43])[C:18]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:8][C:9](=[O:10])[NH:11][CH3:12])=[C:34]([O:39][CH2:40][CH3:41])[CH:33]=1)=[N:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]=[C:29]([CH3:31])[O:28][N:27]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 154907452-Bromo-N-methylacetamideHCID 136366385{2-(3-Ethoxy-4-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

Product 1

HCID 72312806{2-(3-Ethoxy-4-methylcarbamoylmethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterYield 90.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 200 mg of potassium carbonate and 78 mg of 2-bromo-N-methyl-acetamide to a solution of 154 mg of {2-(3-ethoxy-4-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 1 ml of acetone, the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layers were combined and washed with 0.5N hydrochloric acid and saturated brine in that order. The organic layer 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 (161 mg) as a yellow solid.

Workup

  1. washwashed with 0.5N hydrochloric acid and saturated brine in that order
  2. dry with materialThe organic layer was 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-1a64b428e9364d3b9d46b91886012daa
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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