Ammonium Hydroxide → HCID 178502021, compound

HRID 1197843Notes

Reaction equation

HRID 1197843 reaction equation
Cl[CH:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]1[CH:16]=[CH:15][C:6]2[NH:7][C:8]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[N:9][C:5]=2[CH:4]=1.[OH-].[NH4+:24]>O1CCCC1>[NH2:24][CH:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]1[CH:16]=[CH:15][C:6]2[NH:7][C:8]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[N:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 178502019HCID 178502019, compound

Product 1

HCID 178502021HCID 178502021, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above hydrochloride salt of methyl (±)-[5- [chloro (phenyl)methyl]-1H-benzimidazol-2-yl]carbamate was then suspended in dry tetrahydrofuran (30 mL) and excess ammonium hydroxide was added to this suspension. The resulting reaction mixture was stirred at room temperature for 12 hours. The solvent was then removed and the residue was chromatographed on silica gel 60F254 (40 g, 70-230 mesh, column size 1'×1") using CHCl3 :CH3OH (95:5) as eluant. Fractions 3 through 12 (20 mL each) upon concentrating on a steam bath under vacuum afforded the title product, yield 22%; mp>232° C.; IR (KBr): 3340, 1718, 1630, 1600, 870, 750, 721, 695 cm-1. 1H-NMR (DMSO-d6): δ 3.75 (2, 3H, --OCH3); 5.23 (2, 1H, CH--N), 5.60-6.87 (m, 2H, NH2 [exchangeable with D2O]), 6.90-7.83 (m, 9H, Ar--H and NHCO [exchangeable with D2O]). Analysis calculated for C16H16N4O2 : C, 64.85; H, 5.44; N, 18.91 and found: C, 65.03; H, 5.53; N, 18.67.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was then removed
  3. customthe residue was chromatographed on silica gel 60F254 (40 g, 70-230 mesh, column size 1'×1")
  4. concentrationFractions 3 through 12 (20 mL each) upon concentrating on a steam bath under vacuum

Sources & evidence

ORD record
ord-8f4d179457b74c9a9d7d6a190f8addf0
Source dataset
uspto-grants-1994_01
Patent number
US05278181

Reaction notes

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