Dichloromethane → N-ethoxycarbonylmethylthioethyl-N-n-butylcinnamamide

HRID 1707261Notes

Reaction equation

HRID 1707261 reaction equation
C([C:5]1[CH:6]=[C:7]([CH:13]=[C:14](C(C)(C)C)[C:15]=1O)[CH:8]=[CH:9][C:10]([OH:12])=O)(C)(C)C.[CH2:21]([O:23][C:24]([CH2:26][S:27][CH2:28][CH2:29][NH:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:25])[CH3:22].Cl.C(N=C=NCCCN(C)C)C.ClCCl>O>[CH2:21]([O:23][C:24]([CH2:26][S:27][CH2:28][CH2:29][N:30]([CH2:31][CH2:32][CH2:33][CH3:34])[C:10](=[O:12])[CH:9]=[CH:8][C:7]1[CH:6]=[CH:5][CH:15]=[CH:14][CH:13]=1)=[O:25])[CH3:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86747655N-ethoxycarbonylmethylthioethyl-n-butylamine

Product 1

HCID 67822768N-ethoxycarbonylmethylthioethyl-N-n-butylcinnamamideYield 105%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 5.53 g of 3,5-di-t-butyl-4-hydroxycinnamic acid, 4.4 g of N-ethoxycarbonylmethylthioethyl-n-butylamine, and 4.0 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) were added to 100 ml of dichloromethane and the mixture was agitated for 3 hours at room temperature. Then, this reaction mixture was poured into water, and after chloroform extraction the chloroform layer was dehydrated with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue so obtained was separated and purified by column chromatography on silica gel with chloroform, after which hexane was added and crystallization yielded 7.34 g of an N-ethoxycarbonylmethylthioethyl-N-n-butylcinnamamide derivative (yield 79.5%) in the form of white crystals.

Workup

  1. extractionafter chloroform extraction the chloroform layer
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue so obtained
  4. customwas separated
  5. custompurified by column chromatography on silica gel with chloroform
  6. additionafter which hexane was added
  7. customcrystallization

Sources & evidence

ORD record
ord-e338a67485a94dc6b47cab5fe2542b78
Source dataset
uspto-grants-1994_10
Patent number
US05352677

Reaction notes

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