Diethylethanolamine → N-Decyl-3-(3-[cis-3-(2-[N,N-diethylamino]ethoxycarbonyl)propenamido]phenyl)propenamide

HRID 848560Notes

Reaction equation

HRID 848560 reaction equation
[CH2:1]([NH:11][C:12](=[O:29])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:28])/[CH:23]=[CH:24]\[C:25]([OH:27])=[O:26])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:42]([N:44]([CH2:47][CH2:48]O)[CH2:45][CH3:46])[CH3:43]>O1CCCC1>[CH2:1]([NH:11][C:12](=[O:29])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:28])/[CH:23]=[CH:24]\[C:25]([O:27][CH2:43][CH2:42][N:44]([CH2:47][CH3:48])[CH2:45][CH3:46])=[O:26])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 7497Diethylethanolamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 86738051N-Decyl-3-(3-[cis-3-carboxypropenamido]phenyl)propenamide

Product 1

HCID 86738054N-Decyl-3-(3-[cis-3-(2-[N,N-diethylamino]ethoxycarbonyl)propenamido]phenyl)propenamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 800 mg. of N-decyl-3-(3-[cis-3-carboxypropenamido]phenyl)propenamide in 25 ml. of tetrahydrofuran is added 357 mg. of carbonyldiimidazole. The mixture is heated under reflux for 10 minutes, and then 258 mg. of 2-(N,N-diethylamino)ethanol is added. The mixture is again heated under reflux for 10 minutes, and then an additional 258 mg. of 2-(N,N-diethylamino)ethanol is added. The mixture is heated under reflux for 15 minutes and then it is cooled to room temperature. The solvent is removed by evaporation in vacuo, and the residue is dissolved in 75 ml. of ethyl acetate. The ethyl acetate solution is washed successively with water, 1 N sodium hydroxide, water and saturated sodium chloride solution. The ethyl acetate solution is then dried and evaporated in vacuo to give the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 10 minutes
  3. temperatureThe mixture is again heated
  4. temperatureunder reflux for 10 minutes
  5. temperatureThe mixture is heated
  6. temperatureunder reflux for 15 minutes
  7. customThe solvent is removed by evaporation in vacuo
  8. dissolutionthe residue is dissolved in 75 ml
  9. washThe ethyl acetate solution is washed successively with water, 1 N sodium hydroxide, water and saturated sodium chloride solution
  10. dry with materialThe ethyl acetate solution is then dried
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-2c0479c796ca48ca913a949144e53954
Source dataset
uspto-grants-1981_10
Patent number
US04296129

Reaction notes

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