Sodium Hydroxide → HCID 15830090, compound

HRID 1680189Notes

Reaction equation

HRID 1680189 reaction equation
[OH-].[Na+].Cl.Cl.[CH3:5][C:6]1[N:11]=[C:10]([CH2:12][S:13]C(=N)N)[CH:9]=[CH:8][CH:7]=1>O>[CH3:5][C:6]1[N:11]=[C:10]([CH2:12][SH:13])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23457312HCID 23457312, compound

Product 1

HCID 15830090HCID 15830090, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of sodium hydroxide pellets (37 g) in distilled water (140 cc) is added dropwise, in the course of 15 minutes, to a solution, cooled to 15° C., of 2-(6-methylpyrid-2-ylmethyl)isothiourea dihydrochloride (114.7 g) in distilled water (280 cc). The reaction mixture is heated to the boil and is then stirred for 35 minutes. After cooling to 20° C., the reaction mixture is extracted three times with diethyl ether (480 cc in total). The combined ether extracts are washed three times with distilled water (300 cc in total), dried over anhydrous sodium sulphate and concentrated under reduced pressure (20 mm Hg) at 30° C. 6-Methylpyrid-2-ylmethanethiol (55.4 g) is thus obtained in the form of a yellow oil.

Workup

  1. temperatureThe reaction mixture is heated to the boil
  2. extractionthe reaction mixture is extracted three times with diethyl ether (480 cc in total)
  3. washThe combined ether extracts are washed three times with distilled water (300 cc in total)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure (20 mm Hg) at 30° C

Sources & evidence

ORD record
ord-59b0273f942c41a5aa791bad52a260dc
Source dataset
uspto-grants-1981_06
Patent number
US04272534

Reaction notes

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