Ethanol, 2-(cyclohexylamino)- → N-cyclohexyl-N-(2-hydroxyethyl)-gamma-bromocrotonamide

HRID 1903185Notes

Reaction equation

HRID 1903185 reaction equation
[Br:1][CH2:2]/[CH:3]=[CH:4]/[C:5](Cl)=[O:6].[OH:8][CH2:9][CH2:10][NH:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(OCC)C>[CH:12]1([N:11]([CH2:10][CH2:9][OH:8])[C:5](=[O:6])/[CH:4]=[CH:3]/[CH2:2][Br:1])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 17827Ethanol, 2-(cyclohexylamino)-HCID 11263885(E)-4-Bromo-2-butenoyl Chloride

Product 1

HCID 20468037N-cyclohexyl-N-(2-hydroxyethyl)-gamma-bromocrotonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into 100 ml of diethylether was added 19 g of γ-bromocrotonylchloride, while the mixture was stirred at 0°-10° C., 25 g of N-(2-hydroxyethyl)cyclohexylamine was added dropwise. After the addition then the reaction mixture was stirred at the same temperature for 3 hours. The reaction mixture was extracted with ether and the ether extract was washed with 2 N-HCl, a diluted NaHCO3 aqueous solution saturated with NaCl, and water in this order. The organic layer was dried with anhydrous Na2SO4 and the solvent was removed by distillation. 17.5 Grams of N-cyclohexyl-N-(2-hydroxyethyl)-γ-bromocrotonamide was obtained as an oil substance. The chemical stracture of this substance was identified by the NMR spectrum and the data of elementary analysis.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred at the same temperature for 3 hours
  3. extractionThe reaction mixture was extracted with ether
  4. extractionthe ether extract
  5. washwas washed with 2 N-HCl
  6. dry with materialThe organic layer was dried with anhydrous Na2SO4
  7. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-cbba29cc1a4449718883efa158c9c445
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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