1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 4-(methylcarbamoyl)cinnamate

HRID 581763Notes

Reaction equation

HRID 581763 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)(O)=[O:2].Cl.CN.[CH2:19]([N:21]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.O.CN(C)C=O>[CH3:19][NH:21][C:1]([C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)=[O:2]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 54440358Methyl 4-carboxycinnamate

Product 1

HCID 53693514Methyl 4-(methylcarbamoyl)cinnamateYield 48.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-carboxycinnamate (160 mg) in methylene chloride was added methylamine hydrochloride (58 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (140 mg) at ambient temperature, and the mixture was stirred for 2 hours. To this suspension was added 1-hydroxybenzotriazole (137 mg) and dimethylformamide (2 ml), and the mixture was stirred for 14 hours at same temperature. The reaction mixture was poured into water, and extracted with dichloromethane. The organic layer was washed with aqueous sodium bicarbonate solution and water, dried over magnesium sulfate, and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give methyl 4-(methylcarbamoyl)cinnamate (82 mg) as a colorless powder. mp: 210.5° C.

Workup

  1. stirringthe mixture was stirred for 14 hours at same temperature
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with aqueous sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ce050b9d28d8497092d8a88bedf594a4
Source dataset
uspto-grants-1999_07
Patent number
US05922711

Reaction notes

Loading…