Dicyclohexylcarbodiimide → HCID 57042600, compound

HRID 569307Notes

Reaction equation

HRID 569307 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]([CH2:21][CH2:22][O:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:30])[CH:5]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[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]([CH2:21][CH2:22][O:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:30])[CH:5]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 57096431HCID 57096431, compound

Product 1

HCID 57042600HCID 57042600, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

{[(5,6-Dichloro-3-oxo-2,3,9,9a-tetrahydro-9a-(2-trifluoroacetoxyethyl)-1H-fluoren-7-yl]oxy}acetamide (3.65 g, 10 mMole) is dissolved in pyridine (25 ml) an 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 to provide the [(5,6-dichloro-3-oxo-2,3,9,9a-tetrahydro-9a-(2-trifluoroacetoxyethyl)-1H-fluoren-7-yl)oxy]acetonitrile.

Workup

  1. additionis added portionwise over 30 minutes
  2. stirringThe mixture is then stirred at ambient temperature for 3 hours
  3. customThe precipitated dicyclohexylurea is removed by filtration
  4. customthe pyridine removed from the filtrate by evaporation in vacuo

Sources & evidence

ORD record
ord-cc5bf2fce64e4705a14451a6fadbb6bd
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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