Dicyclohexylcarbodiimide → HCID 53698851, compound

HRID 1252629Notes

Reaction equation

HRID 1252629 reaction equation
[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4]([CH:16]=[CH:17][C:18]([OH:20])=O)=[CH:3]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:46][N:47]1[CH2:51][CH2:50][NH:49][C:48]1=[O:52]>CN(C)C=O>[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][NH:5][C:4]([CH:16]=[CH:17][C:18]([NH:46][N:47]2[CH2:51][CH2:50][NH:49][C:48]2=[O:52])=[O:20])=[CH:3]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1816971-Aminoimidazolidin-2-oneHCID 54235107HCID 54235107, compound

Product 1

HCID 53698851HCID 53698851, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2pyridinyl-]-2-propenoic acid (10.85 g), 1 g of N-hydroxybenzotriazole, 0.01 g of N,N-dimethylaminopyridine and 8.24 g of dicyclohexylcarbodiimide were stirred for 30 minutes in 100 ml of dimethylformamide. After cooling to 0° C., 4 g of N-aminoimidazolidinone was added and stirring continued for 1 hour at 0° C. and 10 hours at room temperature. The resulting suspension was then heated to 60° C. and filtered. It was again suspended in 50 ml of dimethylformamide and heated to 60° C. and filtered again. The combined filtrates were evaporated at 40° C. (oil vacuo). The oily residue was stirred with 50 ml of water containing 2 g of sodium bicarbonate. After the filtration, the solid was washed with water, acetone and ether. 12.3 g of solid was obtained after drying. It was stirred together with 8 g of p-toluenesulfonic acid in 100 ml of dichloromethane for 1 hour. Filtration yielded 12.98 g of a white solid. This material was suspended in water. Recrystallization from water/dimethylformamide yielded 8.49 g of the title compound, melting point 271° C.

Workup

  1. temperatureThe resulting suspension was then heated to 60° C.
  2. filtrationfiltered
  3. temperatureheated to 60° C.
  4. filtrationfiltered again
  5. customThe combined filtrates were evaporated at 40° C. (oil vacuo)
  6. stirringThe oily residue was stirred with 50 ml of water containing 2 g of sodium bicarbonate
  7. filtrationAfter the filtration
  8. washthe solid was washed with water, acetone and ether

Sources & evidence

ORD record
ord-8b3a54649f3b459cab85c7b9e72b2f24
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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