Chloroform → HCID 18681088, compound

HRID 1699632Notes

Reaction equation

HRID 1699632 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.C(Cl)(Cl)Cl.[NH2:22][C:23]1[CH:49]=[CH:48][C:26]([CH2:27][N:28]2[C:32]3[CH:33]=[C:34]([C:37](=[O:46])[NH:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=4)[CH:35]=[CH:36][C:31]=3[N:30]=[C:29]2[CH3:47])=[CH:25][CH:24]=1>O>[C:8]1([S:14]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([CH2:27][N:28]3[C:32]4[CH:33]=[C:34]([C:37](=[O:46])[NH:38][CH2:39][C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=5)[CH:35]=[CH:36][C:31]=4[N:30]=[C:29]3[CH3:47])=[CH:48][CH:49]=2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 18680884HCID 18680884, compound

Product 1

HCID 18681088HCID 18681088, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (0.185 g) and benzenesulfonyl chloride (0.210 g) are added to a chloroform (10 ml) solution of 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl) carbamoyl]benzimidazole (0.340 g), and the solution is stirred for eight hours at room temperature. Water is added and the reaction is halted. A chloroform extraction is performed. An organic layer is washed with water (three times), and dried. After concentration, the residue is purified through silica gel column chromatography (eluate: ethyl acetate/methanol=100/0˜4/1), and thus, 1-[4-(benzenesulfonylamino)benzyl]-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole (263) (0.300 g) is obtained. 1H-NMR (CDCl3, δ): 2.53 (3H, s), 4.78 (2H, d, J=4.8 Hz), 5.28 (2H, s), 6.90 (2H, t, J=8.6 Hz), 6.99 (2H, d, J=8.5 Hz), 7.11 (1H, s), 7.23 (1H, dd, J=5.5 and 7.2 Hz), 7.34 (1H, d, J=7.7 Hz), 7.40 (2H, t, J=8.1 Hz), 7.50 (1H, t, J=7.5 Hz), 7.66-7.74 (6H, m), 7.92 (1H, s), 8.56 (1H, d, J=4.8 Hz).

Workup

  1. extractionA chloroform extraction
  2. washAn organic layer is washed with water (three times)
  3. customdried
  4. concentrationAfter concentration
  5. customthe residue is purified through silica gel column chromatography (eluate: ethyl acetate/methanol=100/0˜4/1)

Sources & evidence

ORD record
ord-7acff17e93aa4602b47e8d7c38eb35f1
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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