Ammonium Hydroxide → HCID 178502025, compound

HRID 1197846Notes

Reaction equation

HRID 1197846 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:21]=[CH:20][C:11]3[NH:12][C:13]([NH:15][C:16](=[O:19])[O:17][CH3:18])=[N:14][C:10]=3[CH:9]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26].[NH4+].[OH-]>CO.O>[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6](=[N:25][OH:26])[C:8]2[CH:21]=[CH:20][C:11]3[NH:12][C:13]([NH:15][C:16](=[O:19])[O:17][CH3:18])=[N:14][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 178502028HCID 178502028, compound

Product 1

HCID 178502025HCID 178502025, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl [5-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]carbamate, (581.6 g, 1.86 mole) (Janssen Pharmaceutica, U.S. Pat. No. 3,657,267, Apr. 18, 1972) was suspended in MeOH (15 L) in which hydroxylamine hydrochloride (508.1 g, 7.32 mole) was dissolved. The mixture was heated at reflux (80 hrs) until a clear solution was obtained and the starting material was no longer detected at TLC. After cooling to room temperature, the mixture was filtered to remove undissolved material, and the solvent was removed under reduced pressure to give a solid residue. This material was suspended in H2O (5 L) and adjusted to pH 12 with conc. NH4OH. The title product that was obtained as a precipitate was collected by filtration, washed with H2O, then dried under reduced pressure at 70° C. for 16 hrs. Yield: 620.8 g. TLC Rf=0.4-0.6 (2nd spot), 0.0 (base line material). Mp:>315° C.; 3405, 1725, 1660-1640, 1600, 835, 760 cm-1, 1H NMR (DMSO-d6): δ 3.78 (s, 3 H, OCH3), 6.70-8.00 (m, 7 H, Ar--H), 11.20 (bs, 1 H, NH), 11.90 (bs, 1 H, OH).

Workup

  1. dissolutionwas dissolved
  2. temperatureThe mixture was heated
  3. temperatureat reflux (80 hrs) until a clear solution
  4. customwas obtained
  5. filtrationthe mixture was filtered
  6. customto remove undissolved material
  7. customthe solvent was removed under reduced pressure
  8. customto give a solid residue

Sources & evidence

ORD record
ord-089ead07abba40f29a2f85affe7a2ee5
Source dataset
uspto-grants-1994_01
Patent number
US05278181

Reaction notes

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