3,4-Dimethylbenzaldehyde → HCID 72490709, compound

HRID 968853Notes

Reaction equation

HRID 968853 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[CH3:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[CH3:19])[CH:14]=O>C(OCC)(=O)C>[CH3:10][C:11]1[CH:12]=[C:13]([CH:14]=[N:3][NH:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH:16]=[CH:17][C:18]=1[CH3:19]

Participants

4

Reactant 2

HCID 222783,4-DimethylbenzaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 72490709HCID 72490709, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of t-butyl carbazate (5.06 g, 38.3 mmol) in ethyl acetate (15 mL) was added with stirring 3,4-dimethylbenzaldehyde (5.20 mL, 5.26 g, 39.2 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 (8.76 g, 92.1%): mp 167.7-168.6° C. 1H NMR (DMSO-d6) δ 10.82 (s, 1H), 7.92 (s, 1H), 7.36 (s, 1H), 7.28 (d, 2H, J=3 Hz), 7.14 (d, 2H, J=3 Hz), 2.206 (s, 3H), 2.20 (s, 3H) 1.44 (s, 9H); 13C NMR (DMSO-d6) δ 153.0, 144.1, 138.5, 137.3, 132.9, 130.5, 128.1, 124.8, 79.9, 28.8, 19.99, 19.97; IR (KBr mull) 3361, 3009, 2981, 2981, 1513, 1495 cm−1. A portion was further purified by recrystallization from ethyl acetate for analysis. Anal. Calcd. for C14H20N2O2: C, 67.71; H, 8.12; N, 11.28. Found: C, 67.51; H, 8.07; N, 11.22.

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-857aa673c361415dbc2c0b9caf955fca
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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