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

HRID 1513228Notes

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-c3f7597d68304448974bf55db9f09052
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217065B2

Reaction notes

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