3,4-Dichloroaniline → 42174-34-5

HRID 2354322Notes

Reaction equation

HRID 2354322 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].C(N(CC)CC)C.[C:17](Cl)(=[O:26])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:17](=[O:26])/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 8471TriethylamineHCID 5354261Cinnamoyl Chloride

Product 1

HCID 540351042174-34-5Yield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dichloroaniline (5.41 g, 33.6 mmol) and triethylamine (1.5 mL) were dissolved in 160 mL of THF and treated with trans-cinnamoyl chloride (6.71 g, 40.3 mmol) with vigorous stirring at room temperature for 2 h, and then quenched with 10 mL of H2O. The reaction mixture was 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 white crystalline solid (6.2 g, 63%), MS (ES) m/e 293 [M+H]+.

Workup

  1. customquenched with 10 mL of H2O
  2. extractionThe reaction mixture was extracted 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-304ecd08be5040dfb81cfeaaefd9a1d9
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

Loading…