Triethylamine → HCID 178513236, compound

HRID 1919745Notes

Reaction equation

HRID 1919745 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].C(N(CC)CC)C>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]([NH:20][OH:21])=[NH:18])=[CH:16][C:10]=3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochloride2×HCID 178509510HCID 178509510, compound

Product 1

HCID 178513236HCID 178513236, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-Fluoro-phenyl)-1H-benzoimidazole-5-carbonitrile (1.898 g, 8 mmol; example 1), hydroxylamine hydrochloride (3.34 g, 48 mmol) and triethylamine (5.67 g, 56 mmol) were heated at reflux in 85 ml of ethanol for 6 hours. Heating was continued for further 6 hours after addition of 3 equivalents of hydroxylamine hydrochloride and triethylamine each and molecular sieve (3 Å). The molecular sieve was filtered, the solvent evaporated and the solid recrystallized from methanol. Yield: 85%. MS: m/e=271.05 (M+H+).

Workup

  1. temperatureHeating
  2. filtrationThe molecular sieve was filtered
  3. customthe solvent evaporated
  4. customthe solid recrystallized from methanol

Sources & evidence

ORD record
ord-447b5f692eeb41b982cb5061b905b5e4
Source dataset
uspto-grants-2012_05
Patent number
US08168665B2

Reaction notes

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