Ethanol → Ethyl 2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]acetate

HRID 847272Notes

Reaction equation

HRID 847272 reaction equation
[NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>O>[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:5][N:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178509208HCID 178509208, compound

Product 1

HCID 351912Ethyl 2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]acetateYield 42.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3.9 g of 2-amino-5-mercapto-1,3,4-thiadiazole, 4.2 g of potassium carbonate and 50 ml of ethanol was gradually added 5 g of ethyl bromoacetate under ice cooling. Then, the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added 200 ml of water followed by extraction with ethyl acetate. After washing with water, the extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The solid obtained was washed with toluene and dried to obtain 2.7 g of ethyl [(5-amino-1,3,4-thiadiazol-2-yl)thio]acetate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washAfter washing with water
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe solid obtained
  6. washwas washed with toluene
  7. customdried

Sources & evidence

ORD record
ord-85c6056e5d4c418fa65e18386d6d89b0
Source dataset
uspto-grants-1992_08
Patent number
US05140046

Reaction notes

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