2-Undecanamine → N-(1-Methyldecyl)-3-(3-Nitrophenyl)propenamide

HRID 66808Notes

Reaction equation

HRID 66808 reaction equation
[NH2:1][CH:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:3].[N+:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24](Cl)=[O:25])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]>O1CCCC1>[CH3:3][CH:2]([NH:1][C:24](=[O:25])[CH:23]=[CH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 1144762-UndecanamineHCID 53411291HCID 53411291, compound

Product 1

HCID 54308912N-(1-Methyldecyl)-3-(3-Nitrophenyl)propenamideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 31.0 g. of 2-aminoundecane in 100 ml. of tetrahydrofuran, was added a solution of 19.0 g. 3-(3-nitrophenyl)propenoyl chloride in 100 ml. of tetrahydrofuran, dropwise, during 75 minutes, at ca. 5° C. After the addition, the mixture was allowed to warm to room temperature, and stirring was continued for 45 minutes. The solvent was removed by evaporation in vacuo, and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was removed, washed successively with 1 N hydrochloric acid and water, and dried. Evaporation of the solvent in vacuo, followed by recrystallization of the residue from hexane, afforded 26 g. (83% yield) of the title product, m.p. 81°-83° C.

Workup

  1. customat ca. 5° C
  2. additionAfter the addition
  3. customThe solvent was removed by evaporation in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe ethyl acetate layer was removed
  6. washwashed successively with 1 N hydrochloric acid and water
  7. customdried
  8. customEvaporation of the solvent in vacuo
  9. customfollowed by recrystallization of the residue from hexane
  10. customafforded 26 g

Sources & evidence

ORD record
ord-a9e956b12b074a24966cdf86825557d1
Source dataset
uspto-grants-1982_08
Patent number
US04343813

Reaction notes

Loading…