Phenol → HCID 519480, compound

HRID 2252258Notes

Reaction equation

HRID 2252258 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CCOCC>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 120874-Cyanobenzoic acid

Product 1

HCID 519480HCID 519480, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

4-Cyano-benzoic acid (10.0 g, 68.0 mmol), phenol (6.40 g, 68.0 mmol), DCC (14.73 g, 71.4 mmol), DMAP (0.25 g, 2.04 mmol) and ether (200 mL) were mixed, and stirred at room temperature for 3 days. Ether was removed. To the residue was added CH2Cl2 (200 mL). The solid was filtered. The filtrate was concentrated, and purified by flash chromatography to give the desired product (12.41 g, 82%). MS (DCI/NH3) m/z 224 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 7.19-7.25 (m, 2H) 7.31 (m, 1H) 7.41-7.50 (m, 2H) 7.807.85 (m, 2H) 8.29-8.34 (m, 2H).

Workup

  1. customEther was removed
  2. additionTo the residue was added CH2Cl2 (200 mL)
  3. filtrationThe solid was filtered
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-5db997dd7d6749db96f0faf76ec7196b
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

Loading…