3,4-Dimethylaniline → HCID 913632, compound

HRID 2354407Notes

Reaction equation

HRID 2354407 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[C:10](Cl)(=[O:19])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:19])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 72483,4-DimethylanilineHCID 5354261Cinnamoyl Chloride

Product 1

HCID 913632HCID 913632, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dimethylaniline (5.20 g, 42.9 mmol) was dissolved in 150 mL of THF and treated with trans-cinnamoyl chloride (7.5 g, 45 mmol) with vigorous stirring at room temperature. After 2 hours the mixture was quenched with 10 mL of H2O and extracted with EtOAc (3×100 mL). The combined organics were washed with saturated solution of Na2CO3, brine, dried over MgSO4 and then concentrated in vacuo to yield the title compound as a pure white crystalline solid (6.2 g, 67%). MS (ES) m/e 252 [M+H]+.

Workup

  1. customAfter 2 hours the mixture was quenched with 10 mL of H2O
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organics were washed with saturated solution of Na2CO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da05b135cd984bcbb6af23f18efcf839
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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