Methyl N-(triethylammoniosulfonyl)carbamate → HCID 25235860, compound

HRID 1513232Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:30])[CH2:9][NH:10][C:11]([C:13]2[CH:29]=[CH:28][C:16]3[N:17]=[C:18]([C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=4[Cl:27])[NH:19][C:15]=3[CH:14]=2)=O)=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:30][C:11]([C:13]3[CH:29]=[CH:28][C:16]4[N:17]=[C:18]([C:20]5[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=5[Cl:27])[NH:19][C:15]=4[CH:14]=3)=[N:10][CH:9]=2)=[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)-2-oxo-ethyl]-amide (310 mg, 0.68 mmol) and Burgess reagent (644 mg, 2.70 mmol) 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 phase was dried, filtered, and the solvent removed under reduced pressure. The residue was purified by chromatography using a gradient of 40-75% heptane/ethyl acetate followed by a second chromatography with dichloromethane/acetone (0-20% gradient) to give the title compound. H1-NMR (DMSO-d6): δ 8.69 (m, broad, 1H), 8.34 (d, J=8.5 Hz, 1H), 8.13 (d, J=8.2, Hz 2H), 8.04 (s, broad, 1H), 7.95 (s, 1H), 7.84 (m, 3H), 7.75 (d, J=8.6 Hz, 2H). MS: m/z 441.9 (M+1); High resolution MS (M+H): theory 440.0124, measured 440.0126.

Workup

extractionextracted with water and brine
customThe organic phase was dried
filtrationfiltered
customthe solvent removed under reduced pressure
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-4bbe9ffc8e424771b0758a13b89834d4
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217065B2

Reaction notes

Loading…