Hydrochloric Acid → HCID 67292403, compound

HRID 1685412Notes

Reaction equation

HRID 1685412 reaction equation
C[O:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([S:9][CH3:10])[CH:8]=1.Cl.[NH+]1C=CC=CC=1.[Cl-].[NH4+].Cl>>[CH3:10][S:9][C:7]1[CH:8]=[C:3]([OH:2])[CH:4]=[N:5][CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 13433419HCID 13433419, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 67292403HCID 67292403, compoundYield 47%

Procedure

1.284 g (8.2 mM) of 3-methoxy-5-methylthiopyridine and 2.87 g (24.8 mM) of pyridinium hydrochloride are heated at 150° C. for 2 hours in a reactor adapted for microwaves. A saturated aqueous solution of ammonium chloride is added to the cooled reaction medium and the pH is adjusted to neutral with 1 N hydrochloric acid solution. The precipitate formed is filtered off, the filtrate is then extracted with ether and the organic phase is dried over sodium sulfate and then concentrated under reduced pressure. The residue obtained is purified by chromatography on silica gel using a dichloromethane/methanol mixture (99/1, then 80/20; v/v) as the eluent to give the expected product with a yield of 47%.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. extractionthe filtrate is then extracted with ether
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by chromatography on silica gel using a dichloromethane/methanol mixture (99/1

Sources & evidence

ORD record
ord-aeb8bd0698dd4e64a8f46411c45581eb
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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