Ethyl Acetate → HCID 178497369, compound

HRID 1945468Notes

Reaction equation

[N+:1]([CH2:4][CH2:5][CH2:6]CC1C=CC=CC=1OCC(O)=O)([O-:3])=[O:2].[CH3:19][O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[C:24]([NH2:29])[CH:23]=1.[C:31]([O:34][CH2:35][CH3:36])(=O)[CH3:32].[C:37](=O)(O)[O-].[Na+]>C[Si](OP(=O)=O)(C)C>[CH3:19][O:20][C:21]([C:22]1[CH:27]=[CH:26][C:25]2[NH:28][C:36]([CH2:35][O:34][C:31]3[CH:32]=[CH:37][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[N:29][C:24]=2[CH:23]=1)=[O:30]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of (4-nitro-butyl-phenoxy)-acetic acid (50 mg, 0.25 mmol) and 3,4-diaminobenzoic acid methyl ester (59 mg, 0.35 mmol) in PPSE was heated at 160° C. for 4 h. At the end of the reaction period, the mixture was taken to ethyl acetate and neutralized with aqueous sodium bicarbonate. The organic layer was separated and the aqueous solution extracted with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (MeOH:MC=0.5:9.5) to afford 2-(4-nitro-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a colorless powder (66.4 mg, 80% yield).

Workup

customAt the end of the reaction period
customThe organic layer was separated
extractionthe aqueous solution extracted with ethyl acetate
dry with materialThe combined extracts were dried over anhydrous MgSO4
filtrationfiltered
customthe solvent was removed with rotary evaporator under reduced pressure
customThe residue was purified by flash chromatography (MeOH:MC=0.5:9.5)

Sources & evidence

ORD record: ord-6849d8d31a4c413eb3added809e8a8e8
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394799B2

Reaction notes

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