Chloroform → HCID 21875764, compound

HRID 724101Notes

Reaction equation

HRID 724101 reaction equation
[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[N:6]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([CH3:21])([CH3:20])[C:18]#[N:19])=[CH:13][CH:12]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1.C(Cl)(Cl)Cl.[C:29]1([CH3:41])[CH:34]=[CH:33][C:32]([S:35]([N:38]=[C:39]=[O:40])(=[O:37])=[O:36])=[CH:31][CH:30]=1.C(N(CC)CC)C>C(O)C.O=[Pt]=O>[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[N:6]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([CH3:21])([CH3:20])[CH2:18][NH:19][C:39]([NH:38][S:35]([C:32]4[CH:33]=[CH:34][C:29]([CH3:41])=[CH:30][CH:31]=4)(=[O:37])=[O:36])=[O:40])=[CH:15][CH:16]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 77703p-Toluenesulfonyl isocyanateHCID 21875900HCID 21875900, compound

Product 1

HCID 21875764HCID 21875764, compoundYield 39.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-[4-(5,6-dichloro-2-ethyl-1H-benzimidazol-1-yl)phenyl]-2-methylpropanenitrile (step 3, 102 mg, 0.28 mmol), PtO2 (one portion), chloroform (0.5 mL) in ethanol (15 mL) was stirred under hydrogen atmosphere (4.5 Kg/cm2) at room temperature. After 8 h, the mixture was filtered through a pad of Celite, and the filtrate was concentrated. The residue was suspended in dichloromethane (10 mL). To the suspension was added p-toluenesulfonyl isocyanate (0.3 mL, 1.96 mmol), and triethylamine (0.3 mL, 2.1 mmol) at room temperature. After 0.5 h, the mixture was concentrated. The residue was dissolved in dichloromethane (100 mL) and washed with 10% aqueous citric acid (50 mL), water (50 mL), and brine (50 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified by preparative TLC (ethyl acetate/hexane=2:1) to give 62 mg (37%) of the title compound as white solids: 1H-NMR (CDCl3) δ 7.83 (1H, s), 7.67 (2H, d, J=9.3 Hz), 7.55 (2H, d, J=9.3 Hz), 7.38–7.22 (4H, m), 7.18 (1H, s), 3.45 (1H, br), 2.76 (2H, q, J=8.4 Hz), 2.34 (3H, s), 1.37 (6H, s), 1.31 (3H, t, J=8.2 Hz).

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. waitAfter 0.5 h
  4. concentrationthe mixture was concentrated
  5. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  6. washwashed with 10% aqueous citric acid (50 mL), water (50 mL), and brine (50 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by preparative TLC (ethyl acetate/hexane=2:1)

Sources & evidence

ORD record
ord-6b1d939d3eae4cf48c3970610e2749b2
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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