Sodium Hydroxide → HCID 21876005, compound

HRID 724185Notes

Reaction equation

HRID 724185 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3[CH:15]=[C:16]([CH3:22])[C:17]([C:20]#[N:21])=[C:18]([CH3:19])[C:13]=3[N:12]=[C:11]2[CH2:23][CH3:24])=[CH:6][CH:5]=1.[OH-:25].[Na+]>OS(O)(=O)=O>[Cl:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14]3[CH:15]=[C:16]([CH3:22])[C:17]([C:20]([NH2:21])=[O:25])=[C:18]([CH3:19])[C:13]=3[N:12]=[C:11]2[CH2:23][CH3:24])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21876482HCID 21876482, compound

Product 1

HCID 21876005HCID 21876005, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-[4-(2-chloroethyl)phenyl]-2-ethyl-4,6-dimethyl-1H-benzimidazole-5-carbonitrile (Example 329, step 6, 997 mg, 2.95 mmol) in c.H2SO4 (50 ml) was stirred at 80° C. for 15 h. The mixture was poured onto ice and was neutralized with NaOH. The mixture was extracted with ethyl acetate (600 ml). The organic layer was washed with brine (300 ml), then dried (Na2SO4). The solvent was removed to afford 871 mg (83%) of the title compound as white solids.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionThe mixture was extracted with ethyl acetate (600 ml)
  3. washThe organic layer was washed with brine (300 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-e5231ee498b14b11a43c01d391ebb9cf
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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