Methanol → Methyl 4-(Benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylate

HRID 2239305Notes

Reaction equation

[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:19]([OH:21])=[O:20])[CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1.S(Cl)(Cl)=O.[CH3:26]O>C(OCC)(=O)C>[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:19]([O:21][CH3:26])=[O:20])[CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-methyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxylic acid (10.0 g, 35.4 mmol, STEP 4 in Example 1), and thionyl chloride (5.2 mL, 7.1 mmol) in methanol (300 mL) was stirred at 80° C. for 3 hours. The mixture was diluted with ethyl acetate, and washed with saturated ammonium chloride aqueous solution. The organic layer was dried over magnesium sulfate, and concentrated in vacuum. The residue was diluted with methanol, filtered to remove the precipitate, and the filtrate was concentrated in vacuum. The resulted solid was washed with dichloromethane to give the title compound as a brown solid (29.8 g, crude), which was used in the next step without further purification. MS (ESI) m/z: 297 (M+H)+, 295 (M−H)−.

Workup

washwashed with saturated ammonium chloride aqueous solution
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated in vacuum
additionThe residue was diluted with methanol
filtrationfiltered
customto remove the precipitate
concentrationthe filtrate was concentrated in vacuum
washThe resulted solid was washed with dichloromethane

Sources & evidence

ORD record: ord-7c690e24aec949af9893321babf744d2
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723321B2

Reaction notes

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