1,2-Dichloroethane → HCID 882710, compound

HRID 1815928Notes

Reaction equation

HRID 1815928 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:36](O)(=[O:39])[CH:37]=[CH2:38]>CCOC(C)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH:5][C:36](=[O:39])[CH:37]=[CH2:38]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6581Acrylic AcidHCID 74472-Methoxy-5-nitroanilineHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 882710HCID 882710, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methoxy-5-nitroaniline (0.4 g, 2.38 mmol) was dissolved into CH2Cl2 (12 ml). To this solution was added EDC (1.37 g, 7.14 mmol), HOBT (964 mg, 7.14 mmol), DIEA (2.07 ml, 11.9 mmol) and acrylic acid (0.65 ml, 9.51 mmol). The reaction mixture was kept at RT for 4 h. The reaction mixture was diluted with EtOAc, washed with water, 1 N HCl, dilute NaHCO3, then brine. The organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography using 2:1 EtOAc/hexanes as the solvent to give N-(2-methoxy-5-nitrophenyl)-acrylamide.

Workup

  1. washwashed with water, 1 N HCl, dilute NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-87167eda6c20415385539b25ab7d3ee3
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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