Nitromethane → (E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamine

HRID 872447

Reaction equation

HRID 872447 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:16]([CH3:19])([O-])=O.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:15][C:12](/[CH:13]=[CH:19]/[NH2:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 6176885-(3,4-Dichlorophenyl)-2-furaldehyde

Product 1

HCID 67170044(E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamineYield 92.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-(3,4-dichlorophenyl)furfural (1.18 g, 4.89 mmol) in acetic acid (30 ml) was added nitromethane (0.535 ml, 9.78 mmol) and ammonium acetate (1.13 g, 14.7 mmol). The reaction mixture was heated at 80° C. for 4.5 h. Cooled reaction mixture was poured onto ice water (30 ml) and thus formed precipitate was filtered, washed with water and dried under vacuum to give 1.15 g (83%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 7.37 (d, 1H), 7.43 (d, 1H), 7.76 (d, 1H), 7.95 (dd, 1H), 8.03 (d, 1H), 8.19 (d, 1H), 8.31 (d, 1H).

Workup

  1. temperatureCooled
  2. customreaction mixture
  3. additionwas poured onto ice water (30 ml) and thus formed precipitate
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d3ec8c8042a2450380a5863f5cd8d24d
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Linked notes

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