Methanol → HCID 178473173, compound

HRID 1646079Notes

Reaction equation

HRID 1646079 reaction equation
O.CO.[SH:4][C:5]1[S:6][C:7]([SH:10])=[N:8][N:9]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>[OH-].[Na+]>[SH:10][C:7]1[S:6][C:5]([S:4][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:9][N:8]=1

Participants

6

Reactant 4

HCID 887Methanol3×HCID 962Water2×HCID 7748Ethyl bromoacetateHCID 178418558HCID 178418558, compound

Product 1

HCID 178473173HCID 178473173, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In a mixture of 9.66 g of sodium hydroxide, 14.6 ml of water, and 122 ml of methanol was dissolved 36.3 g of 2,5-dimercapto-1,3,4-thiadiazole. After cooling the mixture, a solution of 24.1 ml of ethyl bromoacetate and 24 ml of methanol was added to the mixture below 10° C. The resultant mixture was stirred for 3 hours at room temperature and cooled below 10° C. 43.5 ml of water and 400 ml of 50% methanol were successively added to the reaction mixture, whereby crystals precipitated, and the mixture was allowed to stand overnight at 4° C. The crystals were collected by filtration, washed successively with water and then 50% methanol, and dried to provide 42.5 g of ethyl [(5-mercapto-1,3,4-thiadiazol-2-yl)thio]acetate.

Workup

  1. temperatureAfter cooling the mixture
  2. temperaturecooled below 10° C
  3. customprecipitated
  4. filtrationThe crystals were collected by filtration
  5. washwashed successively with water
  6. dry with material50% methanol, and dried

Sources & evidence

ORD record
ord-02a8294fa7aa492a92008bf1fa53c1a5
Source dataset
uspto-grants-1993_01
Patent number
US05177215

Reaction notes

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