Dichloromethane → Acetic acid 6-carbamoyl-cyclohex-2-enyl ester

HRID 723522Notes

Reaction equation

HRID 723522 reaction equation
[C:1]([O:4][CH:5]=[CH:6][CH:7]=[CH2:8])(=[O:3])[CH3:2].[C:9]([NH2:13])(=[O:12])[CH:10]=[CH2:11].ClCCl>C1(C)C=CC=CC=1.C1(C=CC(O)=CC=1)O>[C:9]([CH:10]1[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=[CH:7][CH2:8][CH2:11]1)(=[O:12])[NH2:13]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6579AcrylamideHCID 151951,3-Butadienyl acetate2×

Product 1

HCID 45091320Acetic acid 6-carbamoyl-cyclohex-2-enyl esterYield 71%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

1-Acetoxy-1,3-butadiene (20.79 g, 0.185 mol) was dissolved in toluene (21 mL). To this was added acrylamide (11.98 g, 0.168 mol) and hydroquinone (0.111 g). The colourless solution was heated at 110° C. for 116 h under argon. More 1-acetoxy-1,3-butadiene (5.67 g, 0.051 mol) was then added, and heating continued for a further 24 h. The solution was cooled then dichloromethane added. This solution was purified by Biotage 75 chromatography twice on silica (2×400 g) to give the title compound as a viscous oil (21.76 g, 71%), which solidified on standing;

Workup

  1. temperatureheating
  2. temperatureThe solution was cooled
  3. customThis solution was purified by Biotage 75 chromatography twice on silica (2×400 g)

Sources & evidence

ORD record
ord-e6ee652cba8e4660b2a9ff0906bd948b
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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