Sodium Chloride → HCID 54126959, compound

HRID 1250203Notes

Reaction equation

HRID 1250203 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH:7]=O.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].N1CCCC1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[Cl-].[Na+]>C1(C)C=CC=CC=1>[C:9]([C:11](=[CH:7][C:6]1[S:5][N:4]=[N:3][C:2]=1[CH3:1])[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 6101p-Toluenesulfonic acidHCID 7764Ethyl cyanoacetateHCID 31268PyrrolidineHCID 27712924-Methyl-1,2,3-thiadiazole-5-carbaldehyde

Product 1

HCID 54126959HCID 54126959, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 50 ml of toluene were added 1.5 g (12 mmol) of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde, 1.5 g (13 mmol) of ethyl cyanoacetate, 0.40 g (6.0 mmol) of pyrrolidine and 0.20 g (1.2 mmol) of tosylic acid. In a reactor equipped with a Dean-Stark dehydrating apparatus, the mixture obtained above was stirred for 2 hours with heating under reflux. After the reaction was completed, a saturated aqueous solution of sodium chloride was added to the reaction mixture, the objective product was extracted with ethyl acetate, the organic layer was washed successively with dilute hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 3:1 mixture of n-hexane and ethyl acetate. Thus, 0.73 g of the objective compound was obtained.

Workup

  1. customIn a reactor equipped with a Dean-Stark
  2. customthe mixture obtained
  3. temperaturewith heating
  4. temperatureunder reflux
  5. extractionthe objective product was extracted with ethyl acetate
  6. washthe organic layer was washed successively with dilute hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. addition3:1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-84bab6e52ba347f3bac7f89f821b4d13
Source dataset
uspto-grants-2002_01
Patent number
US06337341B1

Reaction notes

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