Methanol → HCID 178502639, compound

HRID 1197845Notes

Reaction equation

HRID 1197845 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.[O:25]([NH2:27])[CH3:26].CO.[NH4+].[OH-]>O>[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6](=[N:27][O:25][CH3:26])[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 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 178502028HCID 178502028, compound

Product 1

HCID 178502639HCID 178502639, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl [5-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]carbamate (Janssen Pharmaceutica, U.S. Pat. No. 3,657,267, Apr. 18, 1972) (31.61 g, 0.11 mole) and methoxylamine hydrochloride (0.35 mole) were added to abs. methanol. After heating under reflux for 48 hrs a clear solution was obtained. After 72 hrs this mixture was filtered hot through Celite then allowed to cool to room temperature. Removal of solvent under reduced pressure gave a solid residue. This material was suspended in H2O and adjusted to pH 12 with conc NH4OH. After stirring for 10 min the precipitate was isolated by filtration, washed repeatedly with H2O, then dried at 50° C. under reduced pressure to give the title product as a white solid. Yield: 33.08 g (96%). Mp: 290°-295° C., TLC: Rf=0.66,0.77 (CHCl3 --MeOH,10:1,SiO2) syn and anti isomers. IR (KBr): 3350, 2939, 1735 cm-1. 1H NMR (DMSO-d6): δ 3.73-3.75 (D, 3H, CH3); 3.85-3.87 (d, 3H, CH3); 6.95-7.46 (m, 7H, Ar); 11.74 (brd, s, 2 H, NH).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 48 hrs a clear solution
  3. customwas obtained
  4. filtrationAfter 72 hrs this mixture was filtered hot through Celite
  5. customRemoval of solvent under reduced pressure
  6. customgave a solid residue
  7. customwas isolated by filtration
  8. washwashed repeatedly with H2O
  9. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-d237d2daaa8b446381ab104ecc91b54f
Source dataset
uspto-grants-1994_01
Patent number
US05278181

Reaction notes

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