Acetic Acid → HCID 178425435, compound

HRID 602250Notes

Reaction equation

HRID 602250 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[NH:19][N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1.[CH2:20]([CH2:24][C:25](=O)[CH3:26])[C:21]([CH3:23])=O.CC(O)=O>C(O)C>[CH3:26][C:25]1[N:1]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[NH:19][N:18]=[N:17][N:16]=3)=[CH:5][CH:4]=2)[C:21]([CH3:23])=[CH:20][CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 178509559N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amine

Product 1

HCID 178425435HCID 178425435, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.8 g of (4a) (9.7 mmol), 1.1 g of acetonylacetone (9.7 mmol) and 0.5 mL of glacial AcOH in 50 mL of absolute ethanol are mixed under a nitrogen atmosphere. The mixture is heated to reflux for 6 h, the solvent is evaporated, the residue is redissolved with chloroform and water, the organic phase is washed with water, dried with Na2SO4 and evaporated. Product: 1.7 g. Formula: C20H19N5 (m.w. 329.41). Yield 54%.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 6 h
  3. customthe solvent is evaporated
  4. dissolutionthe residue is redissolved with chloroform and water
  5. washthe organic phase is washed with water
  6. dry with materialdried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-f63bc9f83d7c4c51b63ac394a4aea222
Source dataset
uspto-grants-2011_03
Patent number
US07906501B2

Reaction notes

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