Hydrochloric Acid → 3-Pyridinecarboxylic acid, 2-[(phenylmethyl)thio]-

HRID 414007

Reaction equation

HRID 414007 reaction equation
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>O>[C:14]1([CH2:13][S:1][C:2]2[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 178524460HCID 178524460, compound

Product 1

HCID 7577793-Pyridinecarboxylic acid, 2-[(phenylmethyl)thio]-Yield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

200 parts 2-mercaptonicotinic acid, 970 parts of water, 215 parts of 50% NaOH, and 164 parts of benzyl chloride were combined and the resulting solution was refluxed for 2 hours. After dilution with 2580 parts of water, the solution was acidified with 207 parts of 36% HCl. The resulting slurry was cooled and filtered. The wet cake was washed with water and dried to give 307 parts (97.1%) of 2-(phenylmethylthio)-3-pyridinecarboxylic acid, m.p. 190°-193° C.

Workup

  1. temperaturethe resulting solution was refluxed for 2 hours
  2. temperatureThe resulting slurry was cooled
  3. filtrationfiltered
  4. washThe wet cake was washed with water
  5. customdried

Sources & evidence

ORD record
ord-efa42f0a24d648f6a6467fcab5f00161
Source dataset
uspto-grants-1988_12
Patent number
US04789393

Linked notes

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