Ammonia → HCID 10852098, compound

HRID 382358Notes

Reaction equation

HRID 382358 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18](OC)=[O:19])[C:11]=3[N:10]=2)[CH:6]=[CH:7][CH:8]=1.[NH3:24]>>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([NH2:24])=[O:19])[C:11]=3[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 10786006HCID 10786006, compound

Product 1

HCID 10852098HCID 10852098, compound

Procedure

Following standard procedure C, the acetate salt of methyl 2-(3′-trifluoromethylphenyl)-1-H-benzimidazole-4-carboxylate (134.8 mg, 0.358 mmol) was treated with excess liquid ammonia in a sealed vessel. The product was purified by recrystallisation from methanol, to yield off-white needles. (78 mg, 72%). mp 268-270° C.; Found C 57.68 H 3.82 N 12.96 C15H10F3N3O.0.6CH3OH Requires C 57.74 H 3.82 N 12.95; vmax(cm−1) 3488.83, 3348.86, 3176.45, 1667.66, 1600.93, 1329.63; δH 7.44-7.52 (1H, t), 7.88-8.04 (5H, m), 8.66-8.70 (1H, d), 8.70 (1H, s, 2′ H), 9.3 (1H, br s, NH), 13.6 (1H, br s, NH); m/z (EI) 305 (M+), 288, 260, 145.

Workup

  1. customThe product was purified by recrystallisation from methanol
  2. customto yield off-white needles

Sources & evidence

ORD record
ord-c997f4b87ebb4103a1c9197d1bc91899
Source dataset
uspto-grants-2001_10
Patent number
US06310082B1

Reaction notes

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