Methyl p-toluenesulfonate → HCID 178504105, compound

HRID 1590618Notes

Reaction equation

HRID 1590618 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3=[N:14][CH:15]=[CH:16][N:11]3[CH:10]=2)=[CH:5][CH:4]=1)=[O:2].[S:17]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)([O:20][CH3:21])(=[O:19])=[O:18]>CC#N>[S:17]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)([O-:20])(=[O:19])=[O:18].[CH3:21][SH:13]1[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:10]=[N+:11]2[CH:16]=[CH:15][N:14]=[C:12]12

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 15229609HCID 15229609, compound

Product 1

HCID 178504105HCID 178504105, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.0 g of 2-(4'-formylphenyl)imidazo-[2,1-b]thiazole and 1.0 g of methyl tosylate in 10 ml of dry CH3CN was refluxed for 20 hours. The solution was then evaporated to dryness. The residue was dissolved in hot water and extracted with chloroform to remove excess methyl tosylate. The aqueous layer was evaporated and the residue was recrystallized from acetone. Yield 1.4 gm (77%); mp 195° C.

Workup

  1. temperaturewas refluxed for 20 hours
  2. customThe solution was then evaporated to dryness
  3. dissolutionThe residue was dissolved in hot water
  4. extractionextracted with chloroform
  5. customto remove excess methyl tosylate
  6. customThe aqueous layer was evaporated
  7. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-1b51e88b15c3420eae03e5b45f7cf840
Source dataset
uspto-grants-1993_04
Patent number
US05204352

Reaction notes

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