Sodium Hydroxide → 3-methyl-2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylic acid

HRID 2404283Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

Add 1N sodium hydroxide (6.1 mL, 6.1 mmol) to a suspension of methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate (420 mg, 2.04 mmol) in methanol (10 mL). The suspension turned to a solution upon addition of 1N sodium hydroxide. Stir at 65° C. for 16 hours. Cool to room temperature then concentrate to remove the methanol. Extract the aqueous with ethyl acetate (5 mL). Acidify the aqueous with 2N hydrogen chloride (3 mL) to pH˜2. Concentrate the aqueous layer to a solid. Triturate the solid with water (3 mL). Filter the precipitate and dry under high vacuum to yield the title compound (234 mg, 59%) as a pale brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.28 (s, 3H). 7.01 (d, J=8.21 Hz, 1H), 7.57 (s, 1H), 7.63 (dd, J=8.11, 127 Hz, 1H), 11.19 (s, 1H), 12.60 (s, 1H).

Workup

temperatureCool to room temperature
concentrationthen concentrate
customto remove the methanol
extractionExtract the aqueous with ethyl acetate (5 mL)
concentrationConcentrate the aqueous layer to a solid
customTriturate the solid with water (3 mL)
filtrationFilter the precipitate
customdry under high vacuum

Sources & evidence

ORD record: ord-55ec6ac582bc482580152881bef7b6d5
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802690B2

Reaction notes

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