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.O1CCOCC1.O.Cl>CO.C(Cl)Cl>[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
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
1-Isopropenyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (630 mg, 1.9 mmol) is dissolved in methanol (2.0 mL), 1,4-dioxane (10 mL) and water (2.0 mL). Then 37% HCl (1.6 mL) is added and the reaction mixture is heated at 65° C. for 6 hr. A white solid is formed during the heating. Then water (80 mL) and CH2Cl2 (80 mL) are added. The organic layer is separated and the aqueous layer is extracted with CH2Cl2 (3×50 mL). The organic layers are combined, washed with Sat. NaHCO3 (100 mL), Sat. NH4Cl (100 mL) and water (3×100 mL), dried over MgSO4 and concentrated to give 560 mg (99%) of 1-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one which is used for the next step without further purification.
Workup
- customA white solid is formed during the heating
- customThe organic layer is separated
- extractionthe aqueous layer is extracted with CH2Cl2 (3×50 mL)
- washwashed with Sat. NaHCO3 (100 mL), Sat. NH4Cl (100 mL) and water (3×100 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-20bc20d469ac4646883388ce71cf3c69
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150556B2
Reaction notes
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