Sodium Iodide → HCID 178497366, compound

Reaction equation

Cl[CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:5]=2[N:4]=1.[Na+].[I-].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(#[N:26])C>>[O:21]1[CH2:22][CH2:23][N:18]([NH:26][CH2:2][C:3]2[NH:7][C:6]3[CH:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:5]=3[N:4]=2)[CH2:19][CH2:20]1

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 6342Acetonitrile

HCID 8083Morpholine

HCID 178497357HCID 178497357, compound

Product 1

HCID 178497366HCID 178497366, compoundYield 81%

Procedure

Methyl 2-(chloromethyl)-1H-benzimidazole-5-carboxylate (5) (0.5 g, 2.2 mmole), NaI (30 mg, 0.2 mmole), in 25 ml of anhydrous acetonitrile, add morpholine (0.48 ml, 5.50 mmole) and stir at ambient temperature for 5 hours. The solution was concentrated under reduced pressure and the resulting yellow solid redissolved in dichloromethane (20 ml) and washed with 10 ml of saturated bicarbonate solution. The organics were dried over anhydrous sodium sulfate and then concentrated to yield a fluffy solid (0.5 g, yield 81%) of 6.