3-Mercaptopropionic Acid → HCID 178482013, compound

HRID 1719592Notes

Reaction equation

HRID 1719592 reaction equation
[SH:1][CH2:2][CH2:3][C:4](O)=O.[CH3:7][N:8]1[C:12]([CH2:13]Cl)=[N:11][N:10]=[N:9]1.[OH-:15].[Na+]>CC(C)=O>[CH3:7][N:8]1[C:12]([CH2:13][CH2:4][CH2:3][C:2]([OH:15])=[S:1])=[N:11][N:10]=[N:9]1

Participants

5

Reactant 3

HCID 65143-Mercaptopropionic AcidHCID 14798Sodium HydroxideHCID 122050865-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazole

Product 1

HCID 178482013HCID 178482013, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Mercaptopropionic acid (1.6 g) is dissolved in 1N aqueous sodium hydroxide solution (45 ml) and thereto is added dropwise a solution of 1-methyl-5-chloromethyl-1,2,3,4-tetrazole (15.2 g) in acetone (20 ml) with stirring under ice-cooling. Stirring is continued for 3 hours under ice-cooling. Acetone is distilled off and the residue is acidified with concentrated hydrochloric acid, saturated with sodium chloride and then, extracted with chloroform. The chloroform solution is dried over magnesium sulfate. After chloroform is distilled off, the residue is subjected to column chromatography (Kieselgel 60, made by Merck) by eluting the column with chloroform-methanol (10:1, V/V) to give 3-(1-methyl-1,2,3,4-tetrazol-5-yl)methylthio-propionic acid (2.1 g) as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringStirring
  3. temperaturecooling
  4. distillationAcetone is distilled off
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform solution is dried over magnesium sulfate
  7. distillationAfter chloroform is distilled off
  8. washby eluting the column with chloroform-methanol (10:1, V/V)

Sources & evidence

ORD record
ord-7b4233d7fd47497aab69ed1c835df13c
Source dataset
uspto-grants-1985_09
Patent number
US04540703

Reaction notes

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