Ethanol → Sbb043676

HRID 1252095Notes

Reaction equation

HRID 1252095 reaction equation
C(O)C.[NH2:4][C:5]1[S:6][C:7]([SH:10])=[N:8][N:9]=1.[OH-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>O>[NH2:4][C:5]1[S:6][C:7]([S:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[N:8][N:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 81011-BromohexaneHCID 14798Sodium HydroxideHCID 178509208HCID 178509208, compound

Product 1

HCID 1579472Sbb043676Yield 77.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 190 ml of ethanol and 240 ml of water, 81.5 g of 2-amino-5-mercapto-1,3,4-thiadiazole and 26.9 g of sodium hydroxide were added. To this mixture 99.0 g of 1-bromohexane was added and the resulting mixture was stirred at 60°-70° C. for 2 hours. After cooling, water was added to the mixture and the mixture was filtered. The residue was washed with water, dried under reduced pressure, and recrystallized from an ethanol/hexane mixture. Thus 100.5 g of 2-amino-5-hexylthio-1,3,4-thiadiazole was obtained. m.p. 113°-115° C. Yield 77%.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washThe residue was washed with water
  4. customdried under reduced pressure
  5. customrecrystallized from an ethanol/hexane mixture

Sources & evidence

ORD record
ord-5c2db0debd1f48c0a317cc74015b94a9
Source dataset
uspto-grants-1988_05
Patent number
US04742063

Reaction notes

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