Benzaldehyde → HCID 178482115, compound

HRID 1023872Notes

Reaction equation

HRID 1023872 reaction equation
[NH:1]1[C:5]([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])=[CH:4][N:3]=[CH:2]1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C.C(OCC)(=O)C>[CH:13](=[N:8]/[C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[C:5]1[NH:1][CH:2]=[N:3][CH:4]=1)\[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 14698017HCID 14698017, compound

Product 1

HCID 178482115HCID 178482115, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(1H-imidazol-5-yl)aniline 965 mg, 0.410 mmol) was dissolved in acetic acid (2 mL) and benzaldehyde (43 mg, 0.410 mmol) was added. The reaction was stirred for 1 h at room temperature, diluted with 30 mL ethyl acetate, and extracted with 5% HCl (56 mL from 50 mL water+6 mL 12N HCl). The aqueous layer was basified with K2CO3 (add solid portionwise until PH=7), then extracted with ethyl acetate (30 mL×2). The organic layer was evaporated under reduced pressure and the residue was separated by column chromatography to afford the desired product (9 mg, 0.036 mmol, 9%). 1H NMR (MeOH-d4): 7.11-7.25 (m, 3H), 7.41-7.48 (m, 2H), 7.61-7.67 (m, 2H), 7.78 (s, 1H), 8.32 (s, 1H), 8.39 (s, 1H), 8.83 (s, 1H).

Workup

  1. extractionextracted with 5% HCl (56 mL from 50 mL water+6 mL 12N HCl)
  2. additionadd solid portionwise until PH=7),
  3. extractionthen extracted with ethyl acetate (30 mL×2)
  4. customThe organic layer was evaporated under reduced pressure
  5. customthe residue was separated by column chromatography

Sources & evidence

ORD record
ord-6b89d5f2184a4050bdd56577bb498eb0
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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