Sodium Hydroxide → HCID 22508674, compound

HRID 2229465Notes

Reaction equation

HRID 2229465 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([C:14]([O:16]CC)=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:19].[OH-].[Na+]>C(O)C>[C:14]([C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:6]([CH3:19])[N:5]([CH2:4][C:3]3[CH:20]=[CH:21][C:22]([C:24]4[S:25][CH:26]=[CH:27][CH:28]=4)=[CH:23][C:2]=3[Cl:1])[C:9]=2[CH:10]=1)([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22508760HCID 22508760, compound

Product 1

HCID 22508674HCID 22508674, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-chloro-4-(thiophen-2-yl)benzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole (0.60 g), a 10% aqueous solution of sodium hydroxide (2 ml), and ethanol (5 ml) were mixed and refluxed for 15 minutes under heating. After allowing the solution to cool to room temperature. insoluble matter was removed by filtration with celite. The filtrate was adjusted to pH 6 with 1N hydrochloric acid (about 4 ml). The deposited crystals were collected by filtration, washed with 50% aqueous ethanol, and dried under reduced pressure to obtain the desired compound, 6-carboxy-1-(2-chloro-4-(thiophen-2-yl) benzyl)-2-methylbenzimidazole (0.208 g).

Workup

  1. temperaturerefluxed for 15 minutes
  2. temperatureunder heating
  3. custominsoluble matter was removed by filtration with celite
  4. filtrationThe deposited crystals were collected by filtration
  5. washwashed with 50% aqueous ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-92767642415a45b39af31c1cd5d16e86
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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