Sodium Hydroxide → HCID 178432231, compound

HRID 2404265Notes

Reaction equation

HRID 2404265 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]2[NH:10][C:11]([CH3:13])=[N:12][C:8]=2[CH:7]=[C:6]([C:14]([O:16]C)=[O:15])[CH:5]=1>CO>[Cl:3][C:4]1[C:9]2[NH:10][C:11]([CH3:13])=[N:12][C:8]=2[CH:7]=[C:6]([C:14]([OH:16])=[O:15])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178498030HCID 178498030, compound

Product 1

HCID 178432231HCID 178432231, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Add 2N sodium hydroxide (5 mL, 5 mmol) to a solution of methyl 7-chloro-2-methyl-1H-benzo[d]imidazole-5-carboxylate (280 mg, 1.25 mmol) in methanol (7.5 mL). Stir at 65° C. for 16 hours. The methanol was concentrated in vacuo and the remaining aqueous layer was extracted with ethyl acetate (10 mL). Acidify the aqueous layer to pH˜4 with 1N hydrochloric acid (˜5 mL). A colorless precipitate was filtered and dried under high vacuum to yield the title compound (189 mg, 72%). 1H NMR (400 MHz, CD3OD) δ ppm 2.61 (s, 3H), 7.86 (d. J=1.37 Hz, 1H), 8.08 (d, J=1.17 Hz, 1H).

Workup

  1. concentrationThe methanol was concentrated in vacuo
  2. extractionthe remaining aqueous layer was extracted with ethyl acetate (10 mL)
  3. filtrationA colorless precipitate was filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-02d02a0476974346b7c86efcd0b8c4e9
Source dataset
uspto-grants-2014_08
Patent number
US08802690B2

Reaction notes

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