Methane → (5-nitro-1H-1,3-benzodiazol-2-yl)methanol

HRID 1262225Notes

Reaction equation

HRID 1262225 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11].[C:12](O)(=O)[CH2:13][OH:14].Cl.O.C>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:12]([CH2:13][OH:14])[NH:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 962Water2×HCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 3744471(5-nitro-1H-1,3-benzodiazol-2-yl)methanolYield 100%

Procedure

1,2-Diamino-4-nitrobenzene (5.00 g, 0.0326 mol), glycolic acid (3.72 g, 0.0490 mol), 4.00 M hydrogen chloride in water (13.1 mL, 0.0522 mol), water (13.1 mL, 0.725 mol), and activated charcoal (100 mg) were refluxed overnight. The reaction was cooled to room temperature, filtered and neutralized with aqueous ammonia. The product was filtered and dried in a vacuum desiccator overnight to obtain (6-nitro-1H-benzoimidazol-2-yl)-methanol as a brown solid (6.29 g, 100%). m.p.=157-162° C.; LCMS (m/e) 194 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 10.24 (bs, 1H), 8.39 (d, 1H, J=1.9 Hz), 8.09 (dd, 1H, J=1.9 and 8.8 Hz), 7.66 (d, 1H, J=8.8 Hz), 5.93 (bs, 1H), 4.77 (s, 2H).

Workup

  1. filtrationfiltered
  2. filtrationThe product was filtered
  3. customdried in a vacuum desiccator overnight

Sources & evidence

ORD record
ord-4f64f2e28a814b60805f80529794bf82
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…