Hydrochloric Acid → 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one
Reaction equation
C([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:15]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)[C:5]1=[O:24])(C)=C.CO.Cl>O>[CH3:23][C:22]1[C:15]2[C:14]([CH2:13][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[NH:4][C:5]3=[O:24])=[CH:18][S:17][C:16]=2[CH:19]=[CH:20][CH:21]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
1-Isopropenyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (0.70 g, 2.1 mmol) was treated with MeOH (10 mL) followed by water (10 mL). To this heterogeneous reaction mixture was added 37% hydrochloric acid (5 mL). This reaction mixture was heated to 65° C. for 3 h. The reaction mixture maintained as a heterogeneous mixture with white precipitates. The reaction mixture was extracted with CH2Cl2 (×2). The combined organic phase was washed with water. The organic phase was dried over Na2SO4 and concentrated to afford 0.7 g of the desired product as a white scaly solid.
Workup
- temperatureThe reaction mixture maintained as a heterogeneous mixture with white precipitates
- extractionThe reaction mixture was extracted with CH2Cl2 (×2)
- washThe combined organic phase was washed with water
- dry with materialThe organic phase was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-986ff121ec15476fbfedc7d1fb8da562
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150556B2
Reaction notes
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