Water → 1-[(2,6-Dichloroimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1896446Notes

Reaction equation

HRID 1896446 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[S:10][C:9]2=[N:11][C:12]([Cl:14])=[CH:13][N:8]2[CH:7]=1.Cl[CH2:16][N:17]1[CH2:21][CH:20]([CH2:22][CH2:23][CH3:24])[CH2:19][C:18]1=[O:25].O>O1CCOCC1>[Cl:5][C:6]1[S:10][C:9]2=[N:11][C:12]([Cl:14])=[C:13]([CH2:16][N:17]3[CH2:21][CH:20]([CH2:22][CH2:23][CH3:24])[CH2:19][C:18]3=[O:25])[N:8]2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 157080412,6-Dichloroimidazo[2,1-b]thiazoleHCID 536292161-(Chloromethyl)-4-propylpyrrolidin-2-one

Product 1

HCID 159530901-[(2,6-Dichloroimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-4-propylpyrrolidin-2-oneYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

At room temperature, AlCl3 (0.237 g, 1.78 mmol, 2 eq) is added to a solution of 2,6-dichloroimidazo[2,1-b][1,3]thiazole x172 (0.171 g, 0.89 mmol, 1 eq) and 1-(chloromethyl)-4-propylpyrrolidin-2-one x63 (0.185 g, 1.06 mmol, 1.2 eq) in 1,4-dioxane (25 ml). The mixture is heated at reflux during 2 hours. After cooling, water (20 ml) is added and the aqueous layer is extracted with CH2Cl2 (3×20 ml). The combined organic layers are dried on anhydrous MgSO4, filtered and evaporated under reduced pressure. The crude is purified on silicagel (CH2Cl2/AcOEt: 9/1) yielding 200 mg of 1-[(2,6-dichloroimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-4-propylpyrrolidin-2-one 93 as a white solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux during 2 hours
  3. temperatureAfter cooling
  4. extractionthe aqueous layer is extracted with CH2Cl2 (3×20 ml)
  5. dry with materialThe combined organic layers are dried on anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude is purified on silicagel (CH2Cl2/AcOEt: 9/1)

Sources & evidence

ORD record
ord-9878e719ce2447e1b8253eaf509206a9
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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