1,2-Dichloroethane → N-(4-nitrophenyl)acrylamide

HRID 1815908Notes

Reaction equation

HRID 1815908 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:34](O)(=[O:37])[CH:35]=[CH2:36]>C(Cl)Cl.CCOC(C)=O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:34](=[O:37])[CH:35]=[CH2:36])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6581Acrylic AcidHCID 74754-NitroanilineHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 82198N-(4-nitrophenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitroaniline (0.4 g, 2.9 mmol) was dissolved in CH2Cl2 (15 ml). To this solution was added EDC (1.67 g, 8.7 mmol), HOBT (1.17 g, 8.7 mmol), DIEA (2.5 ml, 14.5 mmol) and acrylic acid (0.79 ml, 11.6 mmol). The reaction mixture was kept at RT for 4.5 h. The reaction mixture was diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO41 filtered, and evaporated in vacuo. The residue was purified by column chromatography using 2:1 EtOAc/hexanes as the solvent to give N-(4-nitrophenyl)-acrylamide.

Workup

  1. washwashed with brine
  2. customThe organic layer was dried over Na2SO41
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-40d4d1016791491a97a33d23b8557570
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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