3-Nitrophenylboronic Acid → 5-(3-Nitro-phenyl)-1,3-dihydro-benzoimidazol-2-one

HRID 844112Notes

Reaction equation

HRID 844112 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]>>[N+:12]([C:15]1[CH:20]=[C:19]([C:2]2[CH:11]=[CH:10][C:5]3[NH:6][C:7](=[O:9])[NH:8][C:4]=3[CH:3]=2)[CH:18]=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 122280605-Bromo-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 97950315-(3-Nitro-phenyl)-1,3-dihydro-benzoimidazol-2-one

Procedure

Prepared from 5-bromo-1,3-dihydro-benzoimidazol-2-one and 3-nitro-phenyl boronic acid in the same fashion as that of Example 5. White solid: mp 324-325° C.; 1H-NMR(DMSO-d6) δ10.8 (s, 2H), 8.4 (m, 1H), 8.15 (d, 1H, J=7.5 Hz), 8.1 (d, 1H, J=7.5 Hz), 7.7 (t, 1H, J=7.5 Hz), 7.35 (d, 1H, J=7.5 Hz), 7.3 (s, 1H), 7.05 (d, 1H, J=7.5 Hz); MS (ES) m/z 254 ([M−H]−, 100%); Anal. Calc. For C13H9N3O3: C, 61.18; H, 3.55; N, 16.46. Found: C, 60.5; H, 3.69; N, 15.53.

Sources & evidence

ORD record
ord-38d4e9ea31c64e398577aabf53540393
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

Loading…