Dicyclohexylcarbodiimide → HCID 86600355, compound

HRID 1359095Notes

Reaction equation

HRID 1359095 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])C=CC(O)=O)([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([N+:29]([O-:31])=[O:30])[CH:23]=1.[OH:32][C:33]1C2N=NNC=2C=[CH:35][CH:34]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:20][C:17]([C:14]1[CH:13]=[C:7]([C:34](=[CH2:35])[C:33]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([N+:29]([O-:31])=[O:30])[CH:23]=2)=[O:32])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:15]=1[OH:16])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acidHCID 34174194-Amino-2-NitrophenolHCID 178418300HCID 178418300, compound

Product 1

HCID 86600355HCID 86600355, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.78 g (6.4 mmoles) of 3,5-di-tert-butyl-4-hydroxycinnamic acid, 0.99 g (6.4 mmoles) of 4-amino-2-nitrophenol, previously diluted in 10 ml of DNMF, 0.86 g (6.4 mmoles) of hydroxybenzotriazol and 1.32 g (6.4 mmoles) of dicyclohexylcarbodiimide are introduced into a 50 ml flask containing 10 ml of THF. The reaction medium is agitated for 15 hours at ambient temperature, the precipitate which appears is filtered and rinsed with ethyl acetate. After concentration of the solution under reduced pressure, the residue is diluted in 20 ml of ethyl acetate and the insoluble part is filtered again. The filtrate is washed with 20 ml of a saturated solution of sodium carbonate followed by 20 ml of water and 20 ml of a saturated solution of sodium chloride. After drying over sodium sulphate, the organic solution is filtered and concentrated to dryness under reduced pressure. The residue is purified on a silica column (eluant: heptane/ethyl acetate: 8/2). The pure fractions are collected and concentrated under vacuum to produce 1.95 g (47%) of the expected compound in the form of a yellow-orange powder. Melting point: 231-232° C.

Workup

  1. additionare introduced into a 50 ml flask
  2. filtrationthe precipitate which appears is filtered
  3. washrinsed with ethyl acetate
  4. additionAfter concentration of the solution under reduced pressure, the residue is diluted in 20 ml of ethyl acetate
  5. filtrationthe insoluble part is filtered again
  6. washThe filtrate is washed with 20 ml of a saturated solution of sodium carbonate
  7. dry with materialAfter drying over sodium sulphate
  8. filtrationthe organic solution is filtered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe residue is purified on a silica column (eluant: heptane/ethyl acetate: 8/2)
  11. customThe pure fractions are collected
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aa20c7f29228456ea6da3c78d3c1c5de
Source dataset
uspto-grants-2003_07
Patent number
US06599903B2

Reaction notes

Loading…