Sodium Hydroxide → HCID 66820844, compound

HRID 386389Notes

Reaction equation

HRID 386389 reaction equation
[C:1]1([N:11]2[C:15]([S:16][CH2:17][C:18]([O:20]CC)=[O:19])=[C:14]([Si:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=[N:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([N:11]2[C:15]([S:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([Si:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=[N:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66820810HCID 66820810, compound

Product 1

HCID 66820844HCID 66820844, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound ethyl 2-(1-(naphthalen-1-yl)-4-(trimethylsilyl)-1H-1,2,3-triazol-5-ylthio)acetate (1 g, 2.6 mmol), aqueous sodium hydroxide solution (10%, 12 mL) and methanol (20 mL) was stirred at reflux for 2 hours. The reaction mixture was then cooled to room temperature and concentrated to a reduced volume. Water was added, the reaction neutralized with aqueous HCl solution (1N) and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give 2-(1-(naphthalen-1-yl)-4-(trimethylsilyl)-1H-1,2,3-triazol-5-ylthio)acetic acid as a solid.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated to a reduced volume
  3. additionWater was added
  4. customthe reaction neutralized with aqueous HCl solution (1N)
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83698244b91d438cbcf0d0fd448ea395
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

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