N,N'-Dicyclohexylurea → HCID 70045794, compound

HRID 1734097Notes

Reaction equation

HRID 1734097 reaction equation
[C:1]([O:5][C:6]([CH:8]=[CH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[BrH:34].Br.[NH2:36][CH2:37][C:38]1[O:42][C:41]([C:43]([O:45][C:46]2[CH:55]=[CH:54][C:53]3[C:48](=[CH:49][CH:50]=[C:51]([C:56](=[NH:58])[NH2:57])[CH:52]=3)[CH:47]=2)=[O:44])=[CH:40][CH:39]=1.C1(NC(NC2CCCCC2)=O)CCCCC1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[BrH:34].[C:1]([O:5][C:6]([CH:8]=[CH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:36][CH2:37][C:38]2[O:42][C:41]([C:43]([O:45][C:46]3[CH:55]=[CH:54][C:53]4[C:48](=[CH:49][CH:50]=[C:51]([C:56](=[NH:57])[NH2:58])[CH:52]=4)[CH:47]=3)=[O:44])=[CH:40][CH:39]=2)=[O:16])=[CH:17][CH:18]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 4277N,N'-Dicyclohexylurea2×HCID 10868Dicyclohexylcarbodiimide2×HCID 13363982HCID 13363982, compoundHCID 537099394-(3-tert-Butoxy-3-oxoprop-1-en-1-yl)benzoic acid

Product 1

HCID 70045794HCID 70045794, compoundYield 40.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 1049PyridineSolventHCID 31374DimethylacetamideSolvent2×

Procedure

In 15 ml of pyridine and 4 ml of N,N-dimethylacetamide (hereinafter abbreviated as DMA) were dissolved 2.0 g of 4-(2-t-butoxycarbonylvinyl)benzoic acid and 0.1 g of 4-dimethylaminopyridine (hereinafter abbreviated as DMAP) and the solution was stirred while cooling with ice. Then, 1.99 g of N,N'-dicyclohexylcarbodiimide (hereinafter abbreviated as DCC) was added to the mixture obtained above. The mixture was stirred at the same temperature for 30 minutes and then 3.49 g of 6-amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrobromide was added thereto. The reaction mixture was stirred for 3 hours while cooling with ice and then overnight at room temperature, and the precipitated N,N'-dicyclohexylurea (hereinafter abbreviated as DCU) was separated by filtration and washed with a small amount of DMA. The filtrate was added dropwise to 800 ml of ether while stirring and cooling with ice. After the precipitate formed had sedimented, the supernatant was removed by decantation, then 400 ml of acetone was added to the residue and the mixture was stirred for 1 hour at room temperature. After repeating the procedure twice, the precipitated crystals were collected by filtration to obtain 1.88 g of the intended product.

Workup

  1. temperaturewhile cooling with ice
  2. additionwas added to the mixture
  3. customobtained above
  4. stirringThe mixture was stirred at the same temperature for 30 minutes
  5. stirringThe reaction mixture was stirred for 3 hours
  6. temperaturewhile cooling with ice
  7. customovernight
  8. customat room temperature
  9. customwas separated by filtration
  10. washwashed with a small amount of DMA
  11. additionThe filtrate was added dropwise to 800 ml of ether
  12. stirringwhile stirring
  13. temperaturecooling with ice
  14. customAfter the precipitate formed
  15. customthe supernatant was removed by decantation
  16. addition400 ml of acetone was added to the residue
  17. stirringthe mixture was stirred for 1 hour at room temperature
  18. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ca50f415db51463f86e1dcd0959129c7
Source dataset
uspto-grants-1996_07
Patent number
US05532267

Reaction notes

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