Hydrochloric Acid → HCID 71186095, compound

HRID 709067Notes

Reaction equation

HRID 709067 reaction equation
[CH2:1]([C:3]1[CH:24]=[CH:23][C:6]([CH2:7][S:8][C:9]2[CH:10]=[C:11]([O:19]COC)[C:12](=[O:18])[N:13](COC)[CH:14]=2)=[CH:5][CH:4]=1)[CH3:2].Cl>O1CCOCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C:9]2[CH:10]=[C:11]([OH:19])[C:12](=[O:18])[NH:13][CH:14]=2)=[CH:23][CH:24]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867315275-[(4-ethylbenzyl)sulfanyl]-3-(methoxymethoxy)-1-(methoxymethyl)pyridin-2(1H)-one2×

Product 1

HCID 71186095HCID 71186095, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-[(4-ethylbenzyl)sulfanyl]-3-(methoxymethoxy)-1-(methoxymethyl)-pyridin-2(1H)-one (253 mg, 0.724 mmol) (Intermediate 17) in hydrogen chloride solution (4 M in dioxane; 2.10 ml, 8.50 mmol) and dioxane (2 ml) was heated under reflux overnight. The reaction mixture was concentrated in vacuo and the resulting solid was recrystallised in boiling ethanol/water. The resulting recrystallised solid was filtered and dried to yield 5-[(4-ethylbenzyl)sulfanyl]-3-hydroxypyridin-2(1H)-one (45 mg, 0.17 mmol, 20% yield).

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulting solid was recrystallised
  4. customThe resulting recrystallised solid
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-372cb9aded27488ab5c7d6a42fb880bd
Source dataset
uspto-grants-2015_11
Patent number
US09180122B2

Reaction notes

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