Sodium Hydroxide → HCID 178447317, compound

HRID 1410198Notes

Reaction equation

HRID 1410198 reaction equation
C([O:3][C:4]([C:6]1[C:30]([Cl:31])=[CH:29][C:9]2[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH2:20][NH:21][C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[CH:17]=[CH:16][C:15]=3[Cl:28])[NH:12][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+]>CCO>[C:24]([C:22]([NH:21][CH2:20][C:18]1[CH:17]=[CH:16][C:15]([Cl:28])=[C:14]([NH:13][C:11]2[NH:12][C:8]3[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:30]([Cl:31])=[CH:29][C:9]=3[N:10]=2)[CH:19]=1)=[O:23])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468557HCID 178468557, compound

Product 1

HCID 178447317HCID 178447317, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Ethyl-2-[5-(tert.butylcarbonylaminomethyl)-2-chlorophenylamino]-6-chloro-benzimidazole-5-carboxylate (0.91 g, 1.9 mmol) in 20 ml EtOH was treated with 1 N NaOH (3.9 ml+0.98 ml+0.98 ml) for 4 h at rt, for 5 h at 50° C. and for 3 d at rt. The mixture was concentrated, diluted with H2O, acidified with 1 N HCl and cooled in an ice bath. The precipitate was filtered, washed with ice water and dried to give the sub-title compound. Yield 0.81 g (95%).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. temperaturecooled in an ice bath
  4. filtrationThe precipitate was filtered
  5. washwashed with ice water
  6. customdried

Sources & evidence

ORD record
ord-42e8a78e68ab4e87847a094b17747e33
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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