Dicyclohexylcarbodiimide → HCID 14514294, compound

HRID 569285Notes

Reaction equation

HRID 569285 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([CH2:16][C:17]([NH2:19])=O)[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:20][CH2:21][CH3:22])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:23])[CH:5]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([CH2:16][C:17]#[N:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:20][CH2:21][CH3:22])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:23])[CH:5]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 14514293HCID 14514293, compound

Product 1

HCID 14514294HCID 14514294, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

(5,6-Dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren-7-yl)acetamide (7.03 g, 20 mMole) is dissolved in pyridine (50 ml) and 1,3-dicyclohexylcarbodiimide (4.35 g, 21.1 mMole) in pyridine (25 ml) is added with stirring at 15°-20° C. over a period of 30 minutes. The mixture is stirred at 20° C. for 3 hours and the precipitated dicyclohexylurea removed by filtration and the filtrate concentrated in vacuo to remove the pyridine. Addition of water gave the nitrile which is extracted with ether, dried over MgSO4 and the solvent evaporated to give the pure nitrile.

Workup

  1. stirringThe mixture is stirred at 20° C. for 3 hours
  2. customthe precipitated dicyclohexylurea removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customto remove the pyridine
  5. additionAddition of water

Sources & evidence

ORD record
ord-c21fa24dd3c64710a81192e8416914a1
Source dataset
uspto-grants-1988_03
Patent number
US04731472

Reaction notes

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