Potassium Carbonate → 1-Benzothiazol-5-yl-3-pyridin-3-ylimidazolidin-2-one

HRID 80030Notes

Reaction equation

HRID 80030 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:15]=[CH:16][C:17]2[S:21][CH:20]=[N:19][C:18]=2[CH:22]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:21]1[C:17]2[CH:16]=[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][C:18]=2[N:19]=[CH:20]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 148342041-(Pyridin-3-yl)imidazolidin-2-oneHCID 190067695-Iodo-1,3-benzothiazole

Product 1

HCID 596361731-Benzothiazol-5-yl-3-pyridin-3-ylimidazolidin-2-oneYield 61.76%

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: 93.67 mg, 0.5747 mmol) was reacted with 5-iodo-benzothiazole (150 mg, 0.5747 mmol), 1,4-dioxane (5 mL), copper iodide (10.9 mg, 0.05747 mmol), trans-1,2-diamino cyclohexane (19.65 mg, 0.1724 mmol) and potassium carbonate (159 mg, 1.1494 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 105 mg of the product (61.76% 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-85ca62210fa74d3783b81be162ba430f
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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