Diclofenac → HCID 21520576, compound

HRID 1282916Notes

Reaction equation

HRID 1282916 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.[Na].[Cl:8][C:9]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([OH:21])=[O:20]>C1C=CC=CC=1>[N:11]1[CH:10]=[CH:9][CH:25]=[CH:24][C:1]=1[CH2:2][O:20][C:19](=[O:21])[CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][C:10]1[C:9]([Cl:8])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:26]

Participants

5

Reactant 3

HCID 3033DiclofenacHCID 65578Oxalyl chlorideHCID 5360545Sodium

Product 1

HCID 21520576HCID 21520576, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

While stirring, a mixture of 10 ml of oxalyl chloride and 20 ml of anhydrous benzene is added at 5°-10°C to a suspension of 10.0 g of the sodium salt of [o-(2,6-dichloro-anilino)-phenyl]-acetic acid in 100 ml of anhydrous benzene. The reaction mixture is then stirred for 3 hours at room temperature and the suspension is concentrated to dryness at 40°C and 11 Torr. The residue is treated with 40 ml of anhydrous benzene and the mixture is concentrated to dryness under 11 Torr. The residue, [o-(2,6-dichloro-anilino)-phenyl]-acetic acid chloride contaminated with sodium chloride, is treated with 50 ml of anhydrous benzene and, with stirring, subsequently with 2.5 g of 2-hydroxymethyl-pyridine at 10°C. The mixture is stirred for 1 hour at room temperature and concentrated at 40°C/11 Torr. the residue is treated with 150 ml of ether and 30 ml of 2 normal hydrochloric acid. The hydrochloric acid solution is isolated and shaken twice with 50 ml of ether and then made alkaline with 2 normal sodium hydroxide solution. The precipitated oil is dissolved in 50 ml of ether, the ether phase washed twice with 10 ml of water, dried over magnesium sulphate, and concentrated under 11 Torr at 40°C. The residue, [o-(2,6-dichloro-anilino)-phenyl]-acetic acid-(2-pyridyl)-methyl ester, is crystallised from ether/petroleum ether; m.p. 80°-81°C.

Workup

  1. stirringThe reaction mixture is then stirred for 3 hours at room temperature
  2. concentrationthe suspension is concentrated to dryness at 40°C
  3. additionThe residue is treated with 40 ml of anhydrous benzene
  4. concentrationthe mixture is concentrated to dryness under 11 Torr
  5. additionis treated with 50 ml of anhydrous benzene
  6. stirringwith stirring, subsequently with 2.5 g of 2-hydroxymethyl-pyridine at 10°C
  7. stirringThe mixture is stirred for 1 hour at room temperature
  8. concentrationconcentrated at 40°C/11 Torr
  9. additionthe residue is treated with 150 ml of ether and 30 ml of 2 normal hydrochloric acid

Sources & evidence

ORD record
ord-3dd029ca8d6143108d4db93bc0f65e47
Source dataset
uspto-grants-1976_08
Patent number
US03973024

Reaction notes

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