Water → HCID 59497645, compound

HRID 1747279Notes

Reaction equation

HRID 1747279 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].[H-].[Na+].Br[CH2:17][C:18]1[C:19]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=2[S:21][CH:22]=1.O>CN(C=O)C.C(OCC)(=O)C>[Cl:27][C:25]1[CH:24]=[CH:23][C:20]2[S:21][CH:22]=[C:18]([CH2:17][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]3=[O:13])[C:19]=2[CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiophene

Product 1

HCID 59497645HCID 59497645, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-isopropenylbenzimidazolone (0.3 g, 1.72 mmol) in DMF (5 mL) was added 60% NaH (0.1 g, 2.6 mmol). The reaction mixture was stirred at room temperature for 15 min and added 3-(Bromomethyl)-5-chlorobenzo[b]thiophene (0.54 g, 2.07 mmol). The reaction mixture was heated to 65° C. and stirred at that temperature for 2 h. When the reaction was complete, the mixture was treated with water. The mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC to afford 0.53 g (87%) of the desired product.

Workup

  1. temperatureThe reaction mixture was heated to 65° C.
  2. stirringstirred at that temperature for 2 h
  3. washwashed with water (×4)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-e136429283894ac6a9925b20afc9f07e
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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