Water → HCID 178423485, compound

HRID 1503227Notes

Reaction equation

HRID 1503227 reaction equation
[NH:1]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:5]=2[N:4]=1)[NH2:2].[C:13]([CH:16]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17](OCC)=[O:18])(=O)[CH3:14].C(#N)C.O>C(O)(=O)C>[CH3:14][C:13]1[C:16]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:17]([OH:18])[N:1]([C:3]2[NH:7][C:6]3[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:5]=3[N:4]=2)[N:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 246929Ethyl alpha-benzylacetoacetateHCID 178423496HCID 178423496, compound

Product 1

HCID 178423485HCID 178423485, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-hydrazino-5-methyl-1H-benzimidazole (4) (1.0 g) and ethyl 2-acetyl-3-phenylpropanoate (1.4 mL) in acetic acid (20 mL) was stirred at room temperature for 2 hr. The reaction mixture was added to a mixture of acetonitrile (100 mL) and water (100 mL). After stirring at room temperature, the resulting precipitate was collected by filtration, and washed with a mixture of acetonitrile and water (1:1). The precipitate was recrystallized from ethanol (95 mL) to give 3-methyl-1-(5-methyl-1H-benzimidazol-2-yl)-4-(phenylmethyl)-1H-pyrazol-5-ol (5) (0.64 g).

Workup

  1. stirringAfter stirring at room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with a mixture of acetonitrile and water (1:1)
  4. customThe precipitate was recrystallized from ethanol (95 mL)

Sources & evidence

ORD record
ord-9d2ca5df1e8940be891d6d0604f81ef9
Source dataset
uspto-grants-2015_12
Patent number
US09212169B2

Reaction notes

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