Triethylamine → HCID 178513237, compound

HRID 2409252Notes

Reaction equation

HRID 2409252 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([C:20]#[N:21])=[CH:19][C:13]=2[N:12]=1.C(N(CC)CC)C.Cl.[NH2:30][OH:31]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([C:20]([NH:30][OH:31])=[NH:21])=[CH:19][C:13]=2[N:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 178509520HCID 178509520, compound

Product 1

HCID 178513237HCID 178513237, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 2-(2-chloro-5-nitro-phenyl)-1H-benzoimidazole-5-carbonitrile (2.00 g; 6.70 mmol) in ethanol (20 ml) in a sealable tube was added triethylamine (1.90 ml; 13.4 mmol). A solution of hydroxylamine hydrochloride (933 mg; 13.4 mmol) in water (4 ml) was added, the tube sealed and the mixture stirred at 75° C. for 2 hours. After cooling to room temperature, water (100 ml) was added, the precipitate filtered and washed with more water to leave 2-(2-chloro-5-nitro-phenyl)-N-hydroxy-1H-benzoimidazole-5-carboxamidine (1.76 g, 82%).

Workup

  1. customthe tube sealed
  2. temperatureAfter cooling to room temperature
  3. filtrationthe precipitate filtered
  4. washwashed with more water

Sources & evidence

ORD record
ord-016e1101d38045d0a5c83739b6167ab0
Source dataset
uspto-grants-2014_08
Patent number
US08815895B2

Reaction notes

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