Acetic Acid → HCID 178482859, compound

HRID 2092375Notes

Reaction equation

HRID 2092375 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:19])[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1.CC(O)=O>CCO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:18]/[C:15]2[CH:16]=[CH:17][C:12]([N:11]([CH3:19])[CH3:10])=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7472N,N-dimethyl-p-phenylenediamineHCID 77264-Chlorobenzaldehyde

Product 1

HCID 178482859HCID 178482859, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-chloro-benzaldehyde (1.55 g, 11.0 mmol) and N,N-dimethyl-benzene-1,4-diamine (1.5 g, 11.0 mmol) in EtOH (15 ml) was added a catalytic amount of AcOH (0.063 ml, 1.1 mmol) at RT. The reaction mixture was heated at reflux and stirred for 14 h during which time precipitation took place. After cooling to RT, the slurry was filtered and washed with heptane. The solid was collected and dried under high vacuum to yield the title compound (2.09 g, 8.08 mmol, 73%) as a brownish solid. 1H NMR (400 MHz, CDCl3): 3.01 (s, 6H), 6.78 (m, 2H), 7.29 (m, 2H), 7.44 (m, 2H), 7.84 (m, 2H), 8.49 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. filtrationthe slurry was filtered
  4. washwashed with heptane
  5. customThe solid was collected
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-f72fa5a6c25e47c7baeb4dca6e3e0173
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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