Hydrochloric Acid → HCID 178526130, compound

HRID 911653Notes

Reaction equation

HRID 911653 reaction equation
[CH:1]1([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[S:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[CH:1]1([C:8]2[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[S:13])=[CH:16][CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86629665HCID 86629665, compound

Product 1

HCID 178526130HCID 178526130, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add methyl 4-cycloheptylthio-benzoate (1.1 g, 4.16 mmol) and sodium hydroxide (500 mg, 12.5 mmol) to methanol (20 mL) and stir overnight. Add 2M aqueous HCl (20 mL) and extract the aqueous phase with dichloromethane. Wash the combined organic extracts with water (20 mL) and brine (20 mL). Dry the organic solution over Na2SO4, filter and concentrate in vacuo to provide the desired intermediate as a white solid (984 mg, 94%). MS (APCI) m/z: 251 (M+H)+.

Workup

  1. extractionextract the aqueous phase with dichloromethane
  2. washWash the combined organic extracts with water (20 mL) and brine (20 mL)
  3. dry with materialDry the organic solution over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-da21b7a5348f4f97935222748f451676
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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