Methyl chloroformate → [2-(3,4-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester

HRID 2079179Notes

Reaction equation

HRID 2079179 reaction equation
[CH3:1][S:2][C:3](=[NH:28])[CH:4]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[C:15]([CH3:17])[O:14][N:13]=2)=[CH:8][CH:7]=1.N1C(C)=CC(C)=CC=1C.Cl[C:39]([O:41][CH3:42])=[O:40].C(OCC)(=O)C>C1(C)C=CC=CC=1.S(=O)(=O)(O)O.O>[CH3:42][O:41][C:39](=[O:40])[N:28]=[C:3]([S:2][CH3:1])[C:4]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)=[N:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[C:15]([CH3:17])[O:14][N:13]=2)=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 79532,4,6-TrimethylpyridineHCID 8857Ethyl AcetateHCID 595168142-(3,4-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetimidic acid methyl ester

Product 1

HCID 72312776[2-(3,4-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.784 g of 2-(3,4-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetimidic acid methyl ester in 21.1 ml of toluene there were added 0.393 ml of collidine and 0.304 ml of methyl chloroformate under a nitrogen atmosphere, and the mixture was stirred at 80° C. for 15 hours. After cooling the reaction mixture, 150 ml of ethyl acetate and 50 ml of water were added and the pH was adjusted to 4 with a few drops of sulfuric acid. The organic layer was washed with 50 ml of water and 50 ml of saturated brine, 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 (0.436 g) as a light yellow solid.

Workup

  1. additionwere added
  2. washThe organic layer was washed with 50 ml of water and 50 ml of saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-304e506fe0c14ea3ba31d6368ca3e397
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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