Dichloromethane → N-ethoxycarbonylmethylthioethyl-N-n-butylcinnamamide

HRID 487241Notes

Reaction equation

HRID 487241 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-(3dimethylaminopropyl)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-cfc51979bbf84a81b826fb784ea1f31d
Source dataset
uspto-grants-1994_03
Patent number
US05294643

Reaction notes

Loading…