Triethylamine → HCID 178423929, compound

HRID 1016648Notes

Reaction equation

HRID 1016648 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=O)=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:13]=[C:14]([NH2:19])[C:15]([NH2:18])=[CH:16][CH:17]=1.C(N(CC)CC)C>ClCCl>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]2[NH:18][C:6]([C:5]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=3)=[N:19][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103323,4-DiaminotolueneHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 178423929HCID 178423929, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methylbenzoyl chloride (2.17 mL, 2.54 g, 16.4 mmol) in dichloromethane (25 mL) was added dropwise to a stirred, cooled (0° C.) solution of 4-methyl-1,2-benzenediamine (2.0 g, 16.4 mmol) and triethylamine (4.57 mL, 3.32 g, 33 mmol) in dichloromethane (25 mL) and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, acetic acid (40 mL) was added and the mixture was stirred at 100° C. for 24 h. The solvent was evaporated under reduced pressure, water (100 mL) was added and the pH was adjusted to 7.0 with aqueous sodium carbonate (10%). Ethyl acetate (50 mL) was added, the layers were separated and the aqueous layer was extracted with ethyl acetate (4×35 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in ethanol, heated to reflux and allowed to cool. The mixture was filtered and the solvent was evaporated under reduced pressure to give the title compound (1.17 g, 32%). 1H NMR (360 MHz, CDCl3) δ 7.92 (2H, d, J 8.2 Hz), 7.52 (1H, d, J 8.1 Hz), 7.38 (1H, d, J 1.0 Hz), 7.27 (2H, d, J 8.2 Hz), 7.08 (1H, dd, J 8.1, 1.0 Hz), 2.47 (3H, s), and 2.40 (3H, s). m/z (ES+) 223 (M+1).

Workup

  1. customThe solvent was evaporated under reduced pressure, acetic acid (40 mL)
  2. additionwas added
  3. stirringthe mixture was stirred at 100° C. for 24 h
  4. customThe solvent was evaporated under reduced pressure, water (100 mL)
  5. additionwas added
  6. additionEthyl acetate (50 mL) was added
  7. customthe layers were separated
  8. extractionthe aqueous layer was extracted with ethyl acetate (4×35 mL)
  9. washThe combined organic fractions were washed with brine
  10. dry with materialdried (MgSO4)
  11. customthe solvent was evaporated under reduced pressure
  12. dissolutionThe residue was dissolved in ethanol
  13. temperatureheated
  14. temperatureto reflux
  15. temperatureto cool
  16. filtrationThe mixture was filtered
  17. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1168a28788354478ad4cd6edf4b87c12
Source dataset
uspto-grants-2002_11
Patent number
US06476045B2

Reaction notes

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