1-Bromoheptane → 1,3,4-Thiadiazole, 2-amino-5-(heptylthio)-

HRID 1073793Notes

Reaction equation

HRID 1073793 reaction equation
[NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.[OH-].[Na+].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>C(O)C.O>[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 123691-BromoheptaneHCID 14798Sodium HydroxideHCID 178509208HCID 178509208, compound

Product 1

HCID 5344581,3,4-Thiadiazole, 2-amino-5-(heptylthio)-Yield 82.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

In 185 ml of ethanol and 185 ml of water, 68.0 g of 2-amino-5-mercapto-1,3,4-thiadiazole and 22.4 g of sodium hydroxide were added. To this mixture, 84.6 g of 1-bromoheptane was added, and the resulting mixture was warmed to 60° C. and stirred for 2 hours. After cooling, water was added and the mixture was filtered. The residue was washed with water, dried under reduced pressure, and recrystallized from an ethanol/hexane mixture. Thus 90.2 g of 2-amino-5-heptylthio-1,3,4-thiadiazole was obtained. m.p. 112°~113° C. Yield 78%.

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-3e39365279be437890d2df62cf84d2c9
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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