Sodium Hydroxide → HCID 21876005, compound

HRID 1454725Notes

Reaction equation

HRID 1454725 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+]>>[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

3

Reactant 2

HCID 14798Sodium HydroxideHCID 21876482HCID 21876482, compound

Product 1

HCID 21876005HCID 21876005, compoundYield 83%

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 CH2SO4 (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-61117556479641d18e7b4d7a91c3f1ad
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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