Benzaldehyde → HCID 689895, compound

HRID 968847Notes

Reaction equation

HRID 968847 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]=[CH:13][CH:12]=1>C(OCC)(=O)C>[C:11]1([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]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 689895HCID 689895, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of t-butyl carbazate (5.62 g, 42.5 mmol) in ethyl acetate (15 mL) was added with stirring benzaldehyde (4.51 g, 42.5 mmol). Crystallization occurred and the resulting slurry was stirred at rt for 45 min. Hexanes (70 mL) was added and the slurry was 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 (8.34 g, 89.0%): mp 184.1-184.9° C.; 1H NMR (DMSO-d6) δ 10.91 (s, 1H), 7.99 (s, 1H), 7.58 (d, 2H, J=3 Hz), 7.39 (m, 3H), 1.45 (s, 9H); 13C NMR (DMSO-d6) δ 153.0, 143.8, 135.3, 130.0, 129.4, 127.2, 80.1, 28.8; IR (KBr mull) 2983, 1735, 1511, 1157 cm−1; A portion was recrystallized (ethyl acetate) for analysis. Anal. Calcd. For C12H16N2O2: C, 65.43; H, 7.32; N, 12.72. Found: C, 65.16; H, 7.43; N, 12.62.

Workup

  1. customCrystallization
  2. additionHexanes (70 mL) was added
  3. temperaturethe slurry was cooled to 0° C
  4. stirringThe slurry was stirred at 0° C. for 60 min
  5. filtrationfiltered
  6. washrinsed with cold hexanes (20 mL)
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-1e84746bcee748b99bd367e543cfd825
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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