Ammonia → HCID 178488846, compound

HRID 1870937Notes

Reaction equation

HRID 1870937 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]3[C:17]([C:18]([O-:20])=O)=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[NH3:21]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]3[C:17]([C:18]([NH2:21])=[O:20])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 178488848HCID 178488848, compound

Product 1

HCID 178488846HCID 178488846, compoundYield 80%

Conditions

Temperature
100 °C

Procedure

The acetate salt of methyl (2-(4'-methoxyphenyl)benzimidazole-4-carboxylate was dissolved in excess liquid ammonia and heated at 100° C. in a sealed pressure vessel at 40 atmospheres overnight. The ammonia was allowed to evaporate, and the solid residue was collected and washed with ice cold water (3×5 ml). Recrystallisation from aqueous methanol afforded the title compound (226.4 mg, 80%); mp 261-263° C.; Found: C, 66.07; H, 4.23; N, 15.29. C15H13N3O2. 0.2CH3OH requires C, 66.70; H, 5.08; N, 15.35; vmax /cm-1 3321.47, 3140.72, 1656.23, 1608.25, 1421.43, 1242.55; δH (d6DMSO, 200 MHz) 3.96 (3H, s, OMe), 7.23-7.27 (2H, d, J=8.6, Ph-3/3'H), 7.37-7.45 (1H, t, Ar-5H), 7.78-7.82 (1H, d, Ar-4H), 7.87 (1H, br s, Imz-H), 7.93-7.96(1H, d, Ar-6H), 8.27-8.31 (2H, d, J=8.6, Ph-2/2'H), 9.4-9.5 (1H, br s, --CONH), 13.3-13.4 (1H, br s, --CONH); m/z (EI) 267 (M+), 249, 222, 206, 77, 32.

Workup

  1. customto evaporate
  2. customthe solid residue was collected
  3. washwashed with ice cold water (3×5 ml)
  4. customRecrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-a7201f3fc89544ed8b567b5e65a8ccdc
Source dataset
uspto-grants-2000_08
Patent number
US06100283

Reaction notes

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