Dimethyl Sulfoxide → HCID 21875600, compound

HRID 724107Notes

Reaction equation

HRID 724107 reaction equation
[Cl:1][C:2]1[C:3]([C:22]#[N:23])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=3)[C:6]=2[CH:21]=1.CS(C)=[O:26].OO>[OH-].[Na+].CO>[Cl:1][C:2]1[C:3]([C:22]([NH2:23])=[O:26])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][OH:20])=[CH:16][CH:17]=3)[C:6]=2[CH:21]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 21875642HCID 21875642, compound

Product 1

HCID 21875600HCID 21875600, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 6-chloro-2-ethyl-1-[4-(2-hydroxyethyl)phenyl]-1H-benzimidazole-5-carbonitrile (step 4, 2.4 g, 7.4 mmol), DMSO (0.7 mL, 8.8 mmol) and methanol (100 mL) was added 30% aqueous hydrogen peroxide (1.3 mL, 11 mmol) and 0.2 M aqueous NaOH (0.7 mL, 0.14 mmol). The mixture was stirred at 50° C. for 2 h. The solvent was removed and the resulting precipitates were collected by filtration. The precipitates were washed with water and dried under reduced pressure to give 1.9 g (76%) of the title compound as pale pink solids: 1H-NMR (DMSO-d6) δ 7.69 (1H, br.s), 7.61 (1H, s), 7.33–7.40 (4H, m), 6.95 (1H, s), 4.64 (1H, br.s), 3.59 (2H, t, J=6.4 Hz), 2.74 (2H, t, J=6.4 Hz), 2.62 (2H, q, J=7.4 Hz), 1.11 (3H, t, J=7.4 Hz).

Workup

  1. customThe solvent was removed
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. washThe precipitates were washed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-788b3c3ec5904197a659e4360c18646e
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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