Sodium Methoxide → 2-(6-Amino-2-pyridyl)ethanethiol

HRID 566242Notes

Reaction equation

HRID 566242 reaction equation
C([S:4][CH2:5][CH2:6][C:7]1[N:12]=[C:11]([NH2:13])[CH:10]=[CH:9][CH:8]=1)(=O)C.C[O-].[Na+]>CO.Cl>[NH2:13][C:11]1[N:12]=[C:7]([CH2:6][CH2:5][SH:4])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 212658556-(2-Acetylthioethyl)-2-pyridylamine

Product 1

HCID 212657842-(6-Amino-2-pyridyl)ethanethiol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

6-(2-Acetylthioethyl)-2-pyridylamine (0.56 g) was dissolved in methanol (10 ml). To the solution was added, at 0° C., sodium methylate (a 4.9N methanol solution, 0.58 ml), and the mixture was stirred for 30 minutes. To the reaction mixture was added iN hydrochloric acid (2.85 ml), followed by concentration under reduced pressure. To the concentrate was added ethyl acetate (10 ml), which was subjected to extraction. The extract solution was dried over anhydrous magnesium sulfate, followed by concentration to leave the title compound as an oily product (0.43 g).

Workup

  1. additionTo the solution was added, at 0° C.
  2. concentrationfollowed by concentration under reduced pressure
  3. additionTo the concentrate was added ethyl acetate (10 ml), which
  4. extractionwas subjected to extraction
  5. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-96f7ca40286f450c9f28596ebf21dfb0
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Reaction notes

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