Dichloromethane → HCID 18681001, compound

HRID 1699629Notes

Reaction equation

HRID 1699629 reaction equation
Cl[CH2:2]Cl.C[N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14](=[O:23])[NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:13][C:8]=2[N:7]=[CH:6]1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(N(CC)CC)C>[C:24]1([S:30]([N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14](=[O:23])[NH:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)=[CH:13][C:8]=3[N:7]=[C:6]2[CH3:2])(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 18681074HCID 18681074, compound

Product 1

HCID 18681001HCID 18681001, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Dichloromethane (10 ml) and triethylamine (0.760 g) are added to 1-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (1.00 g). Furthermore, benzenesulfonyl chloride (0.994 g) is dripped into the solution. After stirring for three hours, the reaction solution is washed with water three times, and once more washed with a sodium bicarbonate aqueous solution. An organic layer is concentrated under reduced pressure, purified through silica gel column chromatography (eluate: ethyl acetate/ethanol=9/1) and thus, a mixture of 1-benzenesulfonyl-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 1-benzenesulfonyl-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (1.38 g) is obtained. Further, this mixture is purified through medium pressure silica gel column chromatography (eluate: ethyl acetate/methanol=100/3) and thus, 0.550 g of oily 1-benzenesulfonyl-2-Methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole (189) and 0.540 g of oily 1-benzenesulfonyl-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (190) are obtained. The oily materials are dissolved using methylene chloride (1.5 ml), and then crystallized by adding diethylether. 1H-NMR (CDCl3, δ): 2.84 (3H, s), 4.81 (2H, d, J=4.8 Hz), 7.24 (1H, dd, J=5.1 and 7.3 Hz), 7.37 (1H, d, J=7.7 Hz), 7.53 (2H, dd, J=7.9 and 7.5 Hz), 7.63-7.74 (2H, m), 7.85 (1H, dd, J=8.4 and 1.2 Hz), 7.97 (2H, dd, J=9.6 and 1.1 Hz), 8.58-8.61 (2H, m).

Workup

  1. washthe reaction solution is washed with water three times
  2. washonce more washed with a sodium bicarbonate aqueous solution
  3. concentrationAn organic layer is concentrated under reduced pressure
  4. custompurified through silica gel column chromatography (eluate: ethyl acetate/ethanol=9/1)
  5. additionthus, a mixture of 1-benzenesulfonyl-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole

Sources & evidence

ORD record
ord-ea137921e64847f3938b4166db6fe4e6
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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