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

HRID 1084743

Reaction equation

HRID 1084743 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-8b88fdfa35624018abd3cfa1d0d42b15
Source dataset
uspto-grants-1991_04
Patent number
US05006532

Linked notes

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