Potassium Carbonate → 1-Benzothiazol-6-yl-3-pyridin-3-ylimidazolidin-2-one

HRID 80025Notes

Reaction equation

HRID 80025 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:2]=1.I[C:14]1[CH:22]=[CH:21][C:17]2[N:18]=[CH:19][S:20][C:16]=2[CH:15]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:20]1[C:16]2[CH:15]=[C:14]([N:9]3[CH2:10][CH2:11][N:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[C:8]3=[O:12])[CH:22]=[CH:21][C:17]=2[N:18]=[CH:19]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 148342041-(Pyridin-3-yl)imidazolidin-2-oneHCID 226090026-Iodo-1,3-benzothiazole

Product 1

HCID 596361791-Benzothiazol-6-yl-3-pyridin-3-ylimidazolidin-2-oneYield 46.01%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 1, 1-pyridin-3-yl-imidazolidin-2-one (I-1b: 62 mg, 0.3831 mmol) was reacted with 6-iodo-benzothiazole (100 mg, 0.3831 mmol), 1,4-dioxane (10 mL), copper iodide (7 mg, 0.03831 mmol), trans-1,2-diamino cyclohexane (6 mg, 0.5747 mmol) and potassium carbonate (105 mg, 0.7662 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform), afforded 52 mg of the product (46.01% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% MeOH in chloroform)

Sources & evidence

ORD record
ord-7c65583c48e64a1faf68d0675758385e
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…