Hydrochloric Acid → HCID 13102670, compound

HRID 2290396Notes

Reaction equation

HRID 2290396 reaction equation
[OH-].[Na+].[CH2:3]([SH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[C:11]1[C:12]([C:18]([OH:20])=[O:19])=[N:13][C:14](Cl)=[CH:15][CH:16]=1.Cl>CS(C)=O.O>[CH2:3]([S:9][C:11]1[C:12]([C:18]([OH:20])=[O:19])=[N:13][C:14]([S:9][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81061-HexanethiolHCID 14798Sodium HydroxideHCID 15553Clopyralid

Product 1

HCID 13102670HCID 13102670, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

To 300 ml of DMSO was added 84.5 g of powdered NaOH with vigorous stirring followed by the addition of 150 g of n-hexyl mercaptan. The anion of the mercaptan was allowed to form and then 111 g of 3,6-dichloro-2-pyridinecarboxylic acid in 110 ml of DMSO was added through a dropping funnel. The temperature was increased during addition to 135° C. and maintained at that temperature for 21/2 hours. Upon cooling the brown solution was poured into three volumes of water. The resulting solution was acidified with HCl and extracted with 1,1,1-trichloroethane. The organic layer was dried over MgSO4 and the solvent removed on a rotary evaporator. The reaction yielded 155 g (68% yield) of 3,6-bis(n-hexylthio)-2-pyridinecarboxylic acid as a dark oil which solidified on standing; m.p. 40°-42° C.

Workup

  1. customto form
  2. temperaturemaintained at that temperature for 21/2 hours
  3. temperatureUpon cooling the brown solution
  4. extractionextracted with 1,1,1-trichloroethane
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-7f7e5790fe4d4c6ab8531a46da700a99
Source dataset
uspto-grants-1986_10
Patent number
US04616087

Reaction notes

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