Chloroacetonitrile → HCID 20275473, compound

HRID 370750Notes

Reaction equation

HRID 370750 reaction equation
[NH2:1][C:2]1[S:3][C:4](S)=[N:5][N:6]=1.Cl[CH2:9][C:10]#[N:11]>C(O)C>[NH2:1][C:2]1[S:3][C:4]([CH2:9][C:10]#[N:11])=[N:5][N:6]=1

Participants

4

Reactant 2

HCID 7856ChloroacetonitrileHCID 178509208HCID 178509208, compound

Product 1

HCID 20275473HCID 20275473, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-amino-5-mercapto-1,3,4-thiadiazole (66.5 g, 0.50 mol.), and ethanol (500 ml) is heated to reflux and chloroacetonitrile (41.1 g, 0.55 mol.) is added dropwise at reflux. Heating is continued for four hours and then about 400 ml of distillate is removed using a Dean-Stark trap. The clear solution is cooled to about 75° C. and water (150 ml) is added, allowing the temperature to drop to about 50° C. After adjusting the pH to about seven by adding slowly a solution of Na2CO3, the mixture is cooled to room temperature and the gray product is collected by filtration and washed with water. The moist filter cake is recrystallized from 300 ml of ethanol to yield the desired product which melts at 163°-164° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperatureHeating
  5. customabout 400 ml of distillate is removed
  6. additionwater (150 ml) is added
  7. customto drop to about 50° C
  8. additionby adding slowly a solution of Na2CO3
  9. temperaturethe mixture is cooled to room temperature
  10. filtrationthe gray product is collected by filtration
  11. washwashed with water
  12. customThe moist filter cake is recrystallized from 300 ml of ethanol

Sources & evidence

ORD record
ord-adf0095c37d84f628ed1f0b49ab88a0b
Source dataset
uspto-grants-1985_07
Patent number
US04528368

Reaction notes

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