Toluene → HCID 54335975, compound

HRID 622113Notes

Reaction equation

HRID 622113 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[C:5]([CH3:9])[N:4]=[C:3]1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C1(P(=[CH:39][C:40]([O:42][CH3:43])=[O:41])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]1(C)C=CC=CC=1>>[C:40]([CH:39]=[CH:7][C:6]1[N:2]([CH3:1])[C:3]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:4][C:5]=1[CH3:9])([O:42][CH2:43][CH3:44])=[O:41]

Participants

4

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 142571041,4-Dimethyl-5-formyl-2-(4-methoxybenzylthio)imidazole

Product 1

HCID 54335975HCID 54335975, compound

Procedure

A mixture of 1,4-dimethyl-5-formyl-2-(4-methoxybenzylthio)imidazole (1.7 g, 6 mmoles) and methyl (triphenylphosphoranylidene)acetate (4.8 g, 14 mmoles) in toluene (50 ml) was heated to reflux for 16 hours, cooled and concentrated in vacuo. The residue was triturated with ether, filtered and the filtrate was concentrated in vacuo. The residue was chromatographed on silica eluted with hexane-ethyl acetate (3:2) to give 5-[2-(carbethoxy)-ethenyl]-1,4-dimethyl-2-(4-methoxybenzylthio)imidazole (mp 165°-167° C.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was chromatographed on silica
  9. washeluted with hexane-ethyl acetate (3:2)

Sources & evidence

ORD record
ord-752c34e2d3ac48278ec8f8153367bb07
Source dataset
uspto-grants-1988_09
Patent number
US04769386

Reaction notes

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