3-Methoxybenzaldehyde → HCID 2692519, compound

HRID 968823Notes

Reaction equation

HRID 968823 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1>C(OCC)(=O)C>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([CH:10]=[N:3][NH:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 115693-MethoxybenzaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 2692519HCID 2692519, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of t-butyl carbazate (5.59 g, 42.3 mmol) in ethyl acetate (15 mL) was added with stirring m-anisaldehyde (5.17 mL, 5.76 g, 42.3 mmol). Hexanes (70 mL) was added slowly and crystallization occurred. The resulting slurry was stirred at rt for 45 min and then cooled to 0° C. The slurry was stirred at 0° C. for 60 min, then filtered and rinsed with cold hexanes (20 mL), and dried in vacuo at 40° C. to afford the title compound as a solid (9.68 g, 91.4%): mp 135.6-137.4° C.; 1H NMR (DMSO-d6) δ 10.93 (s, 1H), 7.29 (t, 1H, J=8 Hz), 7.14 (d, 2H, J=7 Hz), 6.92 (q, 1H, J=7 Hz), 3.75 (s, 3H), 1.45 (s, 9H); 13C NMR (DMSO-d6) δ 160.2, 153.1, 143.7, 136.8, 130.5, 120.0, 116.2, 111.3, 80.1, 55.7, 28.7; IR (KBr mull): 3360, 3010, 2982, 2838, 1510, 1487 cm−1; A portion was recrystallized from ethyl acetate and submitted for elemental analysis. Anal. Calcd. for C13H18N2O3: C, 62.38; H, 7.25; N, 11.19. Found: C, 62.34.; H, 7.46; N, 11.19.

Workup

  1. customcrystallization
  2. temperaturecooled to 0° C
  3. stirringThe slurry was stirred at 0° C. for 60 min
  4. filtrationfiltered
  5. washrinsed with cold hexanes (20 mL)
  6. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-219cd2e9a61444c7ba087ec5f60cea4b
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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