Dicyclohexylcarbodiimide → HCID 21278783, compound

HRID 2291545Notes

Reaction equation

HRID 2291545 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([NH2:20])=O)[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:22][CH2:23][CH3:24])([C:10]2=[O:21])[CH2:8][CH2:7][C:6](=[O:25])[CH:5]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]#[N:20])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:22][CH2:23][CH3:24])([C:10]2=[O:21])[CH2:8][CH2:7][C:6](=[O:25])[CH:5]=1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 21278782HCID 21278782, compound

Product 1

HCID 21278783HCID 21278783, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

[(5,6-Dichloro-3,9-dioxo-9a-propyl-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]acetamide (3.65 g, 10 mMole) is dissolved in pyridine (25 ml) and N,N'-dicyclohexylcarbodiimide (2.17 g, 10.5 mMole) in pyridine (15 ml) is added portionwise over 30 minutes with stirring at 15°-20° C. The mixture is then stirred at ambient temperature for 3 hours. The precipitated dicyclohexylurea is removed by filtration and the pyridine removed from the filtrate by evaporation in vacuo. Addition of water to the residue gives the product which is dissolved in methylene chloride, dried over MgSO4 and the solvent removed to provide the [(5,6-dichloro-3,9-dioxo-9a-propyl-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]acetonitrile.

Workup

  1. stirringThe mixture is then stirred at ambient temperature for 3 hours
  2. customThe precipitated dicyclohexylurea is removed by filtration
  3. customthe pyridine removed from the filtrate by evaporation in vacuo
  4. additionAddition of water to the residue
  5. customgives the product which
  6. dry with materialdried over MgSO4
  7. customthe solvent removed

Sources & evidence

ORD record
ord-4a2d50cee4324e6185421f8f0b070455
Source dataset
uspto-grants-1989_01
Patent number
US04797391

Reaction notes

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