Hydrochloric Acid → HCID 12269210, compound

HRID 1757992Notes

Reaction equation

HRID 1757992 reaction equation
C1C2C(CCCC2)CCC1.[CH3:11][S:12][C:13]1[C:14](C(O)=O)=[N:15][C:16]([S:19][CH3:20])=[CH:17][CH:18]=1.Cl>>[CH3:20][S:19][C:16]1[CH:17]=[CH:18][C:13]([S:12][CH3:11])=[CH:14][N:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7044Decalin2×HCID 13102669HCID 13102669, compound

Product 1

HCID 12269210HCID 12269210, compoundYield 66%

Conditions

Temperature
175 °C

Procedure

To 75 ml of decahydronaphthalene was added portionwise while heating 59.5 g of 3,6-bis(methylthio)-2-pyridinecarboxylic acid. When the mixture reached 155° C., gas bubbles began to appear. The reaction was heated at 175° C. until no more bubbles appeared. Upon cooling the decahydronaphthalene solution was treated with 40 ml of 6 normal (N) HCl in three portions resulting in the formation of a solid which was collected. The solid was covered with water. The aqueous layer and solid were then made basic with 50% NaOH and extracted with ether. The ether solution was treated with charcoal, dried and the ether removed, which gave 31 g (66% yield) of a yellow oil. A portion of this oil was placed on a Kugelrohr distillation apparatus and the product, 2,5-bis(methylthio)pyridine recovered, at 90° C. at a pressure of 0.1 mm Hg.

Workup

  1. customreached 155° C.
  2. customresulting in the formation of a solid which
  3. customwas collected
  4. extractionextracted with ether
  5. additionThe ether solution was treated with charcoal
  6. customdried
  7. customthe ether removed

Sources & evidence

ORD record
ord-6a1174d202d34c5a95e053f448da513a
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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