Potassium Carbonate → HCID 178456601, compound

HRID 896313Notes

Reaction equation

HRID 896313 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:16]=3[N:15]=2)[C:5]1=[O:30])([CH3:3])=[CH2:2].Cl.[NH2:32][OH:33].C([O-])([O-])=O.[K+].[K+]>CCO>[OH:33][NH:32][C:28]([C:26]1[CH:25]=[CH:24][C:17]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[C:14]([CH2:13][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]3=[O:30])=[N:15][C:16]=2[CH:27]=1)=[NH:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 223492872-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile

Product 1

HCID 178456601HCID 178456601, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile (110 mg, 0.275 mmol) was treated with hydroxylaminehydrochloride (57 mg, 0.275 mmol), K2CO3 (55.3 mg, 0.4 mmol) and heated to reflux in EtOH(10 ml) for 6 h. The solvent was removed and the residue dissolved in CH2Cl2 and washed with H2O. The solvent was removed to give 31 mg (26%) of N-hydroxy-2-(3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxamidine as a white solid.

Workup

  1. temperatureheated
  2. customThe solvent was removed
  3. dissolutionthe residue dissolved in CH2Cl2
  4. washwashed with H2O
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-cb3b0c7cc95d41fcb6b747db2d646c31
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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