Indomethacin → 1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indol acetic acid-2-pyridylmethylthioester

HRID 358036Notes

Reaction equation

HRID 358036 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]([OH:22])=[O:21])=[C:9]2[CH3:23])=[O:7])=[CH:4][CH:3]=1.[SH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][S:26][O:21][C:20](=[O:22])[CH2:19][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:8]([C:6](=[O:7])[C:5]2[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[CH3:23]

Participants

5

Reactant 3

HCID 3715IndomethacinHCID 10868DicyclohexylcarbodiimideHCID 2560712-Pyridinemethanethiol

Product 1

HCID 867395871-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indol acetic acid-2-pyridylmethylthioester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.5 g. (0.018 mol.) of 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indol acetic acid are dissolves in 60 ml. of chloroform. After the addition of 2.9 g. (0.023 mol.) of 2-mercaptomethylpyridine and 4.9 g. (0.023 mol.) of N,N'-dicyclohexyl carbodiimide, the reaction mixture is stirred for 24 hours with the exclusion of moisture. The precipitated material is filtered off and the solvent of the resulting solution is distilled in a vacuum. The resulting residue is subjected to chromatography over a silicic acid gel column using a 1:1-mixture of chloroform and hexane as eluant.

Workup

  1. additionAfter the addition of 2.9 g
  2. filtrationThe precipitated material is filtered off
  3. distillationthe solvent of the resulting solution is distilled in a vacuum

Sources & evidence

ORD record
ord-e8f13e031e7b48eb87bad401a8aaf01f
Source dataset
uspto-grants-1984_08
Patent number
US04464379

Reaction notes

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