Dimethylformamide → Methyl 3-methylthio-2-acetamidocinnamate

HRID 2307892Notes

Reaction equation

HRID 2307892 reaction equation
C(N[C:5](=[CH2:10])[C:6]([O:8][CH3:9])=[O:7])(=O)C.[C:11](=O)([O-])O.[Na+].I[C:17]1[CH:18]=[C:19]([S:23][CH3:24])[CH:20]=[CH:21][CH:22]=1.C[N:26]([CH:28]=[O:29])C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][S:23][C:19]1[C:18]([NH:26][C:28](=[O:29])[CH3:11])=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH:10]=[CH:5][C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 98644Methyl 2-acetamidoacrylateHCID 516892Sodium BicarbonateHCID 107057833-Iodothioanisole

Product 1

HCID 54544409Methyl 3-methylthio-2-acetamidocinnamate

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

4.8 g of methyl (3-methylthio)-2-acetamidocinnamate are obtained in the form of a white solid which melts at 139° C. by proceeding as in Example 34-3 but using 5.6 g of methyl 2-acetamidoacrylate, 0.18 g of palladium acetate, 8.2 g of tetrabutylammonium chloride, 5.86 g of sodium hydrogen carbonate and 6.5 g of 3-iodo-1-methylthiobenzene dissolved in 160 ml of anhydrous DMF.

Sources & evidence

ORD record
ord-edd9731b18df44c79ff3ba6129fcc325
Source dataset
uspto-grants-2004_12
Patent number
US06833382B2

Reaction notes

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