Benzaldehyde → HCID 178482600, compound

HRID 2105224Notes

Reaction equation

HRID 2105224 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH2:10][C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:12]=1>C(Cl)Cl>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH:12]=[C:11]([CH2:10]/[N:9]=[CH:1]/[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:15][N:14]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 28063634HCID 28063634, compound

Product 1

HCID 178482600HCID 178482600, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Freshly distilled benzaldehyde (373 mg, 3.5 mmol) was added to a solution of 5-aminomethyl-3-(pyrid-2-yl)isoxazole (Method 70 of WO 03/048133) (0.614 mg, 3.5 mmol) in dry DCM (18 ml). 4 Å molecular sieve (1.75 g) was then added and the mixture stirred gently under nitrogen for 20 hours. The molecular sieve was removed by filtration and the filtrate evaporated. The residue was dissolved in toluene and the solution concentrated by evaporation. The product crystallised and was collected by filtration to give the title compound (900 mg, 97%).

Workup

  1. addition4 Å molecular sieve (1.75 g) was then added
  2. customThe molecular sieve was removed by filtration
  3. customthe filtrate evaporated
  4. dissolutionThe residue was dissolved in toluene
  5. concentrationthe solution concentrated by evaporation
  6. customThe product crystallised
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-ddbe38f3fb0a46c6bc523f78c8f8dfcb
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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