Acetic Acid → 5-(m-Chlorobenzylmercapto)-2-pyridinecarboxylic acid methyl ester

HRID 259246Notes

Reaction equation

HRID 259246 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][SH:8].[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N+]([O-])=O)=[CH:18][N:17]=1)=[O:15].C(O)(=O)C>CN(C)C=O>[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([S:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([Cl:3])[CH:5]=2)=[CH:18][N:17]=1)=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 111056423-ChlorobenzenemethanethiolHCID 12457882Methyl 5-nitropicolinate

Product 1

HCID 539053865-(m-Chlorobenzylmercapto)-2-pyridinecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the stirred suspension of 1.73 g of sodium hydride in 30 ml of dimethylformamide the solution of 12.7 g of m-chlorobenzylmercaptan is added during 2 minutes and stirring is continued for 15 minutes. Thereupon the solution of 12.25 g of 5-nitro-pyridine-2-carboxylic acid methyl ester in 75 ml of dimethylformamide is added all at once. The mixture is stirred for 1 hour on the steam bath and allowed to stand at room temperature overnight. It is poured onto ice and acetic acid, the suspension obtained filtered and the residue recrystallized from 95% aqueous ethanol, to yield the 5-(m-chlorobenzylmercapto)-2-pyridinecarboxylic acid methyl ester melting at 75°-77°.

Workup

  1. additionis added during 2 minutes
  2. stirringThe mixture is stirred for 1 hour on the steam bath
  3. waitto stand at room temperature overnight
  4. customthe suspension obtained
  5. filtrationfiltered
  6. customthe residue recrystallized from 95% aqueous ethanol

Sources & evidence

ORD record
ord-b060ace6d4344894886171317ff743bb
Source dataset
uspto-grants-1977_07
Patent number
US04036965

Reaction notes

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