Diethyl Ether → HCID 18694253, compound

HRID 1870885Notes

Reaction equation

HRID 1870885 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)=[C:9]([CH3:23])[CH:8]=1.[CH3:24]C(C)([O-])C.[K+].IC.CCOCC>CN(C=O)C.C(OCC)(=O)C.ClCCl>[CH3:24][N:6]1[CH2:5][CH2:4][N:3]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:18]=3)=[C:9]([CH3:23])[CH:8]=2)[C:2]1=[O:1]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 18694248HCID 18694248, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18694253HCID 18694253, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4'-(4,5-dihydro-2-oxoimidazol-1-yl)-2'-methylbiphenyl-4-carboxylate (D18) (0.208 g, 0.67 mmol) was stirred in dry DMF (5 ml). Potassium t-butoxide (0.10 g, 0.82 mmol) and iodomethane (0.065 ml, 1.0 mmol) were added. The mixture was stirred for 1 h, diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated to give a gum. Chromatography on silica eluting with 50% ether in dichloromethane gave the title compound (0.205 g, 94%) as a white solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto give a gum

Sources & evidence

ORD record
ord-b70e9242b6784e76a1b4fc9d405a18ef
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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