Hydrochloric Acid → 1-(4,5,6-Trichloro-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid

HRID 538197Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:15](COCCOC)[C:14]3[CH:22]=[C:23]([Cl:28])[C:24]([Cl:27])=[C:25]([Cl:26])[C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.Cl>C(O)(=O)C>[Cl:26][C:25]1[C:13]2[N:12]=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)[NH:15][C:14]=2[CH:22]=[C:23]([Cl:28])[C:24]=1[Cl:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 1-[4,5,6-trichloro-1-(2-methoxy-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.166 g, 0.372 mmol) and acetic acid (6 mL) was added 6M aq. hydrochloric acid (6 mL). The reaction mixture was heated to 100° C. for 18 h and then cooled to 23° C. The precipitate was collected to yield the titled compound as the HCl salt (0.91 g, 74% yield). MS (ESI/CI): mass calcd. for C11H6Cl3N4O2, 330.0; m/z found, 331.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.92 (s, 1H), 8.34 (s, 1H), 7.74 (s, 1H).

Workup

temperaturecooled to 23° C
customThe precipitate was collected

Sources & evidence

ORD record: ord-2c9bfd2f89864e3c82b1e8d73d0504a9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865713B2

Reaction notes

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