Dicyclohexylcarbodiimide → HCID 9818440, compound

HRID 1884553Notes

Reaction equation

HRID 1884553 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].[C:12]12([C:22](O)=[O:23])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:12]12([C:22]([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:23])[CH2:19][CH:18]3[CH2:17][CH:16]([CH2:15][CH:14]([CH2:20]3)[CH2:13]1)[CH2:21]2

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 132351-Adamantanecarboxylic acidHCID 69860Dimethylbarbituric acid

Product 1

HCID 9818440HCID 9818440, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1,3-dimethylbarbituric acid (5.00 g, 32.05 mmol), 1-adamantanecarboxylic acid (8.65 g, 48.03 mmol), 4-dimethylaminopyridine (1.95 g, 16.01 mmol) in dry CH2Cl2 (30 ml) was cooled to 0° C. and 1,3-dicyclohexylcarbodiimide (7.26 g, 35.22 mmol) added. The reaction mixture was stirred at room temperature overnight and filtered. The solid was washed with CH2Cl2 (150 ml) and the combined solution was washed with 2 N HCl solution (40 ml). The organic phase was dried over MgSO4 and evaporated. The residue was crystallized from MeOH giving 5-(1-adamantanecarbonyl)-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 12 (7.10 g, 69%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with CH2Cl2 (150 ml)
  3. washthe combined solution was washed with 2 N HCl solution (40 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-8718394103134617ae5e44c05a2b1e7e
Source dataset
uspto-grants-2004_07
Patent number
US06765089B1

Reaction notes

Loading…