Fumaric Acid → HCID 22474038, compound

HRID 2183675Notes

Reaction equation

HRID 2183675 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10]3[N:11]4[CH2:19][CH2:18][N:17]=[C:12]4[S:13][C:14]=3[S:15][CH3:16])=[CH:7][CH:8]=[CH:9][C:2]1=2.[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>CO>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10]3[N:11]4[CH2:19][CH2:18][N:17]=[C:12]4[S:13][C:14]=3[S:15][CH3:16])=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 10268863HCID 10268863, compound

Product 1

HCID 22474038HCID 22474038, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(benzo[b]thiophen-4-yl)-2-(methylthio)-5,6-dihydroimidazo[2,1-b]thiazole (5.5 g), fumaric acid (2.1 g) and methanol (32 ml) was heated under reflux for 5 minutes then stirred at ambient temperature for 25 minutes. The resulting solid was collected by filtration, washed with ice-cold methanol (10 ml) and dried in vacuo at 95° C. for 2.5 hours to give 3-(benzo[b]thiophen-4-yl)-2-(methylthio)-5,6-dihydroimidazo[2,1-b]thiazole fumarate (6.4 g) as a colourless solid, m.p. 185-187° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 minutes
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ice-cold methanol (10 ml)
  5. customdried in vacuo at 95° C. for 2.5 hours

Sources & evidence

ORD record
ord-daff810c13c541e49fca05e928c92fa6
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

Loading…