Ammonium Hydroxide → HCID 17952492, compound

HRID 1828181Notes

Reaction equation

HRID 1828181 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([CH2:22][C:23]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=O)[C:13]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)=O)=[CH:11][C:6]=2[N:5]([CH2:31][CH3:32])[C:4]1=[O:33])[CH3:2].C([O-])(=O)C.[NH4+:38].[NH4+].[OH-]>C(O)(=O)C>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[CH:22]=[C:23]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[NH:38][C:13]=3[C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)=[CH:11][C:6]=2[N:5]([CH2:31][CH3:32])[C:4]1=[O:33])[CH3:2]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 17952493HCID 17952493, compound

Product 1

HCID 17952492HCID 17952492, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(1,3-diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-4-pyridin-3-yl-1-m-tolyl-butane-1,4-dione (600 mg, 1.13 mmol) and ammonium acetate (871 mg, 11.3 mmol) in acetic acid (3.77 mL) was heated at 110° C. for 4 hours. The reaction was then poured over a mixture of ice and NH4OH and stirred for 5 minutes. The aqueous mixture was extracted with EtOAc (3×10 mL). The organics were combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo to give a orange oil. The oil was purified by flash chromatography using a gradient of Et2O to 50% EtOAc/Et2O, affording 30 mg of the title compound. MS (M+1)=423.2.

Workup

  1. extractionThe aqueous mixture was extracted with EtOAc (3×10 mL)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a orange oil
  6. customThe oil was purified by flash chromatography

Sources & evidence

ORD record
ord-0cbef19f229944c5ad9472f26c893bf0
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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