Thionyl Chloride → HCID 68421991, compound

HRID 506437Notes

Reaction equation

HRID 506437 reaction equation
[CH:1]1([C:4]2[N:5]=[N:6][S:7][C:8]=2[C:9]([NH2:11])=O)[CH2:3][CH2:2]1.S(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[N:5]=[N:6][S:7][C:8]=2[C:9]#[N:11])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68420889HCID 68420889, compound

Product 1

HCID 68421991HCID 68421991, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Cyclopropyl-1,2,3-thiadiazole-5-carboxamide (4 g; 24 mmols) was dissolved in toluene (15 ml), and thionyl chloride (5 ml) was added thereto, followed by refluxing for 10 hours under heating. After cooling to room temperature, ice was added thereto to stop the reaction, and sodium hydrogen carbonate was added thereto to neutralize, followed by extracting with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to thereby obtain 2.1 g of 4-cyclopropyl-1,2,3-thiadiazole-5-carbonitrile.

Workup

  1. temperatureby refluxing for 10 hours
  2. temperatureunder heating
  3. additionice was added
  4. additionwas added
  5. extractionby extracting with ethyl acetate
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-652de6a6a4654b0b89869e573d324c15
Source dataset
uspto-grants-2010_08
Patent number
US07786040B2

Reaction notes

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