Diclofenac → Diclofenac lactam

HRID 1616722Notes

Reaction equation

HRID 1616722 reaction equation
ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[CH:24]1[CH:29]=[C:28]([CH2:30][C:31](O)=[O:32])[C:27]([NH:34][C:35]2[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:42])=[CH:26][CH:25]=1.CCOC(C)=O>ClCCl>[CH2:30]1[C:31](=[O:32])[N:34]([C:35]2[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:42])[C:27]2[C:28]1=[CH:29][CH:24]=[CH:25][CH:26]=2

Participants

6

Reactant 4

HCID 3033DiclofenacHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 27211Diclofenac lactam

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Hydroxysuccinimide (0.76 mmol) and DCC (0.76 mmol) are added to a solution of the corresponding diclofenac acid derivative (0.506 mmol) dissolved in 10 ml of dichloromethane. The mixture is stirred for 1 hour and monitored by TLC (EtOAc:He, 1:1). When completion of the reaction is detected, the mixture is filtered and the solvent is evaporated under reduced pressure. The crude product is purified by column chromatography to afford the pure diclofenac amide derivative.

Workup

  1. filtrationthe mixture is filtered
  2. customthe solvent is evaporated under reduced pressure
  3. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-681110233dcb459e8c5b5d8b61d5d222
Source dataset
uspto-grants-2014_07
Patent number
US08765815B2

Reaction notes

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