Ethyl Acetate → 6-[5-(4-Chlorophenyl)-4-methyloxazol-2-yl]-2-(2,6-dichlorophenyl)-1H-benzimidazole

HRID 1360731Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:31])[CH:9]([NH:11][C:12]([C:14]2[CH:30]=[CH:29][C:17]3[N:18]=[C:19]([C:21]4[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:28])[NH:20][C:16]=3[CH:15]=2)=O)[CH3:10])=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.C(OCC)(=O)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:31][C:12]([C:14]3[CH:30]=[CH:29][C:17]4[N:18]=[C:19]([C:21]5[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=5[Cl:27])[NH:20][C:16]=4[CH:15]=3)=[N:11][C:9]=2[CH3:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-(2,6-dichlorophenyl)-3H-benzimidazole-5-carboxylic acid [2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-amide (480 mg, 1.02 mmol) and Burgess Reagent (848 mg, 4.06 mmol) in THF (10 mL) was heated in a microwave apparatus at 150° C. for 30 min. The mixture was poured into ethyl acetate and extracted with water and brine. The organic layer was dried, filtered, and the solvent removed under reduced pressure. The residual oil was triturated with acetonitrile to afford the title compound. H1-NMR (DMSO-d6): δ 8.40 (s, broad, 0.5H), 8.22 (s, broad, 0.5H), 8.0 (m, 1H), 7.72 (m, 8H), 2.47 (s, 3H). MS: m/z 455.9 (M+1); High resolution MS (M+H): theory: 454.0281, measured: 454.0279.

Workup

extractionextracted with water and brine
customThe organic layer was dried
filtrationfiltered
customthe solvent removed under reduced pressure
customThe residual oil was triturated with acetonitrile

Sources & evidence

ORD record: ord-525a000ba1904628a9da150b6003e558
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879850B2

Reaction notes

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