Methanol → 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionitrile

HRID 1747331Notes

Reaction equation

HRID 1747331 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:22](#[N:25])[CH:23]=[CH2:24].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO.[NH4+].[Cl-]>CN(C=O)C.O>[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[N:14]([CH2:24][CH2:23][C:22]#[N:25])[C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 7855AcrylonitrileHCID 25517Ammonium ChlorideHCID 66854Benzyltrimethylammonium hydroxideHCID 594973791-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 594975803-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionitrileYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (50 mg, 0.17 mmol) in dry DMF (1.0 mL) are added acrylonitrile (0.012 mL, 0.19 mmol) and 40% benzyltrimethyl ammonium hydroxide in MeOH (0.008 mL, 0.017 mmol). The resulting mixture is stirred at room temperature for 2 hr and then Sat. NH4Cl (2 mL) is added along with water (30 mL). Then the mixture is extracted with EtOAc (3×30 mL). The organic layers are combined, dried over MgSO4 and concentrated to give crude product. Purification by flash column chromatography affords 58 mg (98%) of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionitrile.

Workup

  1. extractionThen the mixture is extracted with EtOAc (3×30 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-2d0195766bd94f9fb645701f64d4c9fe
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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