Decylamine → N-Decyl-3-phenyl-3-(4-nitrophenyl)propenamide

HRID 66618

Reaction equation

HRID 66618 reaction equation
[CH2:1]([NH2:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:12]1([C:18]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[CH:19][C:20](Cl)=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1>[CH2:1]([NH:11][C:20](=[O:21])[CH:19]=[C:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:23]1[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 8916DecylamineHCID 545299323-Phenyl-3-(4-nitrophenyl)propenoyl chloride

Product 1

HCID 53643429N-Decyl-3-phenyl-3-(4-nitrophenyl)propenamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5.89 g. of decylamine in 25 ml. of tetrahydrofuran was added a solution of 4.89 g. of 3-phenyl-3-(4-nitrophenyl)propenoyl chloride in 25 ml. of tetrahydrofuran, dropwise, during 20 minutes, at ice-bath temperature. The solvent was removed by evaporation in vacuo and the residue was partitioned between ethyl acetate and water. The layers were separated, and the ethyl acetate layer was washed with water, dried using sodium sulfate, and then evaporated in vacuo. This afforded 5.6 g. of the title compound, m.p. 91°-93° C.

Workup

  1. customThe solvent was removed by evaporation in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe ethyl acetate layer was washed with water
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-95afdeb0788641779bcbb9277debbf05
Source dataset
uspto-grants-1982_08
Patent number
US04342781

Linked notes

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