N-Methylaniline → HCID 19813254, compound

HRID 466982Notes

Reaction equation

HRID 466982 reaction equation
[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[C:6]([C:13]([O:15]C(OCC)=O)=O)[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8].[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[S:3]1[CH:4]=[CH:5][S:1][C:2]1=[C:6]([C:13](=[O:15])[N:22]([CH3:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([O:9][CH:10]([CH3:11])[CH3:12])=[O:8]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 19813261HCID 19813261, compound

Product 1

HCID 19813254HCID 19813254, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropyl 2-(1,3-dithiol-2-ylidene)-2-(ethoxycarbonyloxy-carbonyl)acetate (15.9 g) and N-methylaniline (6.43 g) were dissolved in methylene chloride (100 ml). The solution was stirred at room temperature for 24 hrs. The resultant mixture was washed with aqueous sodium hydroxide solution, dil-HCl and water. After removal of solvent the residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (9:1) as an eluent to give the product (13.2 g, 78.7%) as a yellow oil.

Workup

  1. washThe resultant mixture was washed with aqueous sodium hydroxide solution
  2. customAfter removal of solvent the residue
  3. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6c4e57128f174820b69eaa837296eafc
Source dataset
uspto-grants-1992_10
Patent number
US05158950

Reaction notes

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