Potassium Carbonate → 1-Isopropenyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

HRID 1747285Notes

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].C[N+](C)(C)[CH2:16][C:17]1[C:18]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:19]=2[S:20][CH:21]=1.[I-].C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C>[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:16][C:17]2[C:18]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:19]=3[S:20][CH:21]=2)[C:5]1=[O:13])([CH3:3])=[CH2:2]

Participants

Conditions

Temperature: 120 °C

Procedure

1-isopropenylbenzimidazolone (0.5 g, 2.9 mmol) in DMA (8 mL) was added and trimethyl-(4-methyl-benzo[b]thiophen-3-ylmethyl)-ammonium; iodide (1.0 g, 2.9 mmol) and K2CO3 (0.80 g, 5.74 mmol). The reaction mixture was heated to 120° C. for 15 min in a microwave and then 150° C. for another 5 min. The mixture was 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 using 98:2 CH2Cl2:MeOH as an eluent to afford 0.7 g of the desired product as a white solid

Workup

washwashed with water (×4)
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated
customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record: ord-554c0506cc914ec3b3fe943da6f6fd27
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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