Water → HCID 18681088, compound

HRID 276061Notes

Reaction equation

HRID 276061 reaction equation
C(N(CC)CC)C.[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:18][C:19]1[CH:45]=[CH:44][C:22]([CH2:23][N:24]2[C:28]3[CH:29]=[C:30]([C:33](=[O:42])[NH:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH:31]=[CH:32][C:27]=3[N:26]=[C:25]2[CH3:43])=[CH:21][CH:20]=1.O>C(Cl)(Cl)Cl>[C:8]1([S:14]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][N:24]3[C:28]4[CH:29]=[C:30]([C:33](=[O:42])[NH:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=5)[CH:31]=[CH:32][C:27]=4[N:26]=[C:25]3[CH3:43])=[CH:44][CH:45]=2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 18680884HCID 18680884, compound

Product 1

HCID 18681088HCID 18681088, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.185 g) and benzenesulfonyl chloride (0.210 g) were added to a solution of 0.340 g of 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]-benzimidazole in 10 ml of chloroform, and the mixture was stirred at room temperature for 8 hours. Water was added thereto to stop the reaction, and the reaction mixture was extracted with chloroform. The organic layer was washed three times with water, dried, and concentrated. The residue was then purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 100:1 to 4:1) to give 0.300 g of 1-[4-(benzenesulfonylamino)benzyl]-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole (263).

Workup

  1. customthe reaction
  2. extractionthe reaction mixture was extracted with chloroform
  3. washThe organic layer was washed three times with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was then purified through silica-gel column chromatography (eluent
  7. additiona mixture of ethyl acetate and methanol at a ratio of 100:1 to 4:1)

Sources & evidence

ORD record
ord-a87df751f19d4c45bbf2c1d21aafcc1e
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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