Ethyl propiolate → (E)-3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-acrylic acid ethyl ester

HRID 1747311Notes

Reaction equation

HRID 1747311 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]([O:26][CH2:27][CH3:28])(=[O:25])[C:23]#[CH:24]>C(C#N)(C)=O.CN(C=O)C.CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:27]([O:26][C:22](=[O:25])/[CH:23]=[CH:24]/[N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[C:10]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=3[S:7][CH:8]=2)[C:13]1=[O:21])[CH3:28]

Participants

7

Reactant 2

HCID 12182Ethyl propiolateHCID 594973791-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 59497619(E)-3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-acrylic acid ethyl esterYield 82.4%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 694302-OxopropiononitrileSolvent

Procedure

To a solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (0.1 g, 0.34 mmol) in AcCN (2 mL) and DMF (1 mL) were added ethyl propiolate (0.04 mL, 0.34 mmol) and DMAP (0.02 mL, 0.17 mmol). The reaction mixture was stirred at room temperature for 2 h. When the reaction was complete, the reaction mixture was diluted with CH2Cl2 and washed with water. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 0.11 g of the desired product as a white solid. LCMS (ESMS): m/z 393.13 (M+H+).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-013705c8404a44b3936d326b5018f2b6
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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