Hydrochloric Acid → Diclofenac lactam

HRID 1807433Notes

Reaction equation

HRID 1807433 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]([O-:20])=O.Cl>O>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[N:10]1[C:11]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:17][C:18]1=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86644291HCID 86644291, compound

Product 1

HCID 27211Diclofenac lactam

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 g sodium-[2-(2,6-dichloro-phenylamino)-phenyl]-acetate are dissolved in 6 ml of water, combined with 5.2 ml 1 N hydrochloric acid and the precipitated solid is suction filtered after stirring for 10 minutes. After drying in vacuo the solid is taken up in 6 ml of tetrahydrofuran, combined with 990 μl triethylamine and 1.17 g N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide-hydrochloride and stirred for 3 hours. Then it is divided between water and ethyl acetate, the aqueous phase is extracted twice with ethyl acetate and the combined organic phases are dried on magnesium sulphate. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30 to 20:80).

Workup

  1. filtrationfiltered
  2. customAfter drying in vacuo the solid
  3. stirringstirred for 3 hours
  4. extractionthe aqueous phase is extracted twice with ethyl acetate
  5. customthe combined organic phases are dried on magnesium sulphate
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30 to 20:80)

Sources & evidence

ORD record
ord-bfb737c0ef834d0ba9ca113f7b0b58c1
Source dataset
uspto-grants-2013_01
Patent number
US08357689B2

Reaction notes

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