Sodium Hydroxide → HCID 178494653, compound

HRID 2054485Notes

Reaction equation

HRID 2054485 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([CH2:12][O:13][CH3:14])[NH:11][C:7]=2[C:6]([C:15]([O:17]C)=[O:16])=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([CH2:12][O:13][CH3:14])[NH:11][C:7]=2[C:6]([C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178494654HCID 178494654, compound

Product 1

HCID 178494653HCID 178494653, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of methyl 7-methoxy-2-methoxymethyl-3H-benzimidazole-4-carboxylate [12.12 g, Reference Example 3(a)] in methanol (100 ml) was treated with 2M sodium hydroxide (48 ml). The resulting mixture was heated to 50° C. then stirred at this temperature for 6 hours. The reaction mixture was concentrated to half its original volume then treated with 1M hydrochloric acid (98 ml). The solution was cooled in an icebath and the resulting solid filtered then dried under high vacuum overnight to give the title compound (11.0 g) as a solid. M+236. This material was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated to half its original volume
  2. additionthen treated with 1M hydrochloric acid (98 ml)
  3. temperatureThe solution was cooled in an icebath
  4. filtrationthe resulting solid filtered
  5. customthen dried under high vacuum overnight

Sources & evidence

ORD record
ord-cb90bed955cc473eb0fae57097a683b4
Source dataset
uspto-grants-2008_02
Patent number
US07329675B2

Reaction notes

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