3,4-Dichlorobenzaldehyde → HCID 2692515, compound

HRID 968842Notes

Reaction equation

HRID 968842 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH:14]=O>C(OCC)(=O)C>[Cl: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[Cl:19]

Participants

4

Reactant 2

HCID 227103,4-DichlorobenzaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 2692515HCID 2692515, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of t-butyl carbazate (4.99 g, 37.76 mmol) in ethyl acetate (10 mL) was added with vigorous stirring a solution of 3,4-dichlorobenzaldehyde (6.77 g, 38.6 mmol) in ethyl acetate (10 mL) followed by hexanes (40 mL). Crystallization occurred and the resulting slurry was stirred at rt for 15 min, then cooled to 0° C. and held at that temperature for 45 min. The solids were filtered, rinsed with cold hexanes and dried in vacuo at 60° C. to afford the title compound as a solid (10.10 g, 92.4%): mp 173.8-174.4° C. (dec); 1H NMR (DMSO-d6) δ 11.16 (br s, 1 H), 7.79 (s, 1 H), 7.62 (d, 1 H, J=1.8 Hz), 7.57 (d, 1 H, J=8.5 Hz), 7.55 (m, 1 H), 1.44 (s, 9 H); 13C NMR (DMSO-d6) δ 152.9, 141.1, 136.1, 132.3, 132.1, 131.6, 128.6, 127.0, 80.4, 28.7; IR (KBr mull) 3358, 3010, 2983, 1736, 1508, 1475 cm−1. A portion was recrystallized (ethyl acetate) for analysis. Anal. Calcd. for C12H14Cl2N2O2: C, 49.84; H, 4.88; Cl, 24.52; N, 9.69. Found: C, 49.59; H, 4.71; Cl, 24.43; N, 9.57.

Workup

  1. customCrystallization
  2. temperaturecooled to 0° C.
  3. waitheld at that temperature for 45 min
  4. filtrationThe solids were filtered
  5. washrinsed with cold hexanes
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-9954f5ef150d45a3818eb82c16d34df2
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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