Sodium hydride → 4-(4-Methoxybenzylthio)nicotinic acid

HRID 1200019Notes

Reaction equation

HRID 1200019 reaction equation
Cl[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][SH:18])=[CH:15][CH:14]=1.[H-].[Na+]>CN(C)C=O>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][S:18][C:2]2[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 8182294-Chloronicotinic acid

Product 1

HCID 142776524-(4-Methoxybenzylthio)nicotinic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred and ice-cooled mixture of 788 mg (0.005 mole) 4-chloronicotinic acid [prepared by the process set forth in W. C. J. Ross, J. Chem. Soc.(C), 1816 (1966)] and 771 mg (0.005 mole) of 4-methoxybenzylmercaptan in 6 mL of dry N,N-dimethylformamide was treated with 480 mg (0.012 mole) of 60% sodium hydride dispersion. The reaction was stirred at room temperature for 4 hours during which a thick solid formed, which was taken up in 75 mL of ice water. After extraction with 25 mL of hexane, the aqueous layer was acidified with 2.5N hydrochloric acid to precipitate 4-(4-methoxybenzylthio)-nicotinic acid; yield 1.2 g (89% of theory), m.p. 230° C.

Workup

  1. temperatureice-cooled
  2. customprepared by the process
  3. stirringThe reaction was stirred at room temperature for 4 hours during which a thick solid
  4. customformed
  5. extractionAfter extraction with 25 mL of hexane
  6. customto precipitate 4-(4-methoxybenzylthio)-nicotinic acid

Sources & evidence

ORD record
ord-8d469a7469b3419a8770d8b05bb82be3
Source dataset
uspto-grants-1990_02
Patent number
US04904672

Reaction notes

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