Water → HCID 20081440, compound

HRID 1609441Notes

Reaction equation

HRID 1609441 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[N:12]=[C:11]([NH:17][S:18]([CH:21]([CH:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])(=[O:20])=[O:19])[N:10]=1.IC.O>CN(C)C=O.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[N:12]=[C:11]([N:17]([CH3:1])[S:18]([CH:21]([CH:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])(=[O:20])=[O:19])[N:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 20081442HCID 20081442, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20081440HCID 20081440, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (1.4 g) was added with stirring and cooling to the product of Example 1 (4.0 g) in dimethylformamide (25 ml). Iodomethane (1.78 g) was added portionwise, stirring was continued for 2 hours and the reaction mixture was allowed to stand at room temperature for 8 days. Addition to water and isolation through ethyl acetate gave the crude title product as a yellow oil. Purification by flash chromatography on silica gel in 10% ethyl acetate/dichloromethane gave 2.3 g (55%) pure product as a pale yellow oil.

Workup

  1. stirringstirring
  2. waitto stand at room temperature for 8 days
  3. customgave the crude title product as a yellow oil
  4. customPurification by flash chromatography on silica gel in 10% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-3e9943588b1f4a178446e6b6c0882bff
Source dataset
uspto-grants-1995_03
Patent number
US05401710

Reaction notes

Loading…