Dicyclohexylcarbodiimide → HCID 23506182, compound

HRID 1884549Notes

Reaction equation

HRID 1884549 reaction equation
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[O:4].[CH:12]1[C:24]2[CH:23]([C:25](O)=[O:26])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:12]1[C:24]2[CH:23]([C:25]([CH:8]3[C:9](=[O:10])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:11])[C:6]3=[O:7])=[O:26])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 69860Dimethylbarbituric acidHCID 748099-Carboxyfluorene

Product 1

HCID 23506182HCID 23506182, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1,3-dimethylbarbituric acid (2.5 g, 16.01 mmol), 9-fluorenylcarboxylic acid (5.05 g, 24.01 mmol), 4-dimethylaminopyridine (0.98 g, 8.00 mmol) in dry CH2Cl2 (15 ml) was cooled to 0° C. and 1,3-dicyclohexylcarbodiimide (3.30 g, 16.01 mmol) added. The reaction mixture was stirred at room temperature overnight and filtered. The solid was washed with CH2Cl2 (50 ml) and the combined solution was washed with 2 N HCl solution (5 ml). The organic phase was dried over MgSO4 and evaporated. The residue was crystallised from recrystallised from MeOH giving 5-(9-fluorenyl-carbonyl)-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 5 (2.85 g, 69%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with CH2Cl2 (50 ml)
  3. washthe combined solution was washed with 2 N HCl solution (5 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. customThe residue was crystallised
  7. customfrom recrystallised from MeOH

Sources & evidence

ORD record
ord-07af5f3ab6cb4843810002b39aab699d
Source dataset
uspto-grants-2004_07
Patent number
US06765089B1

Reaction notes

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