Hydrochloric Acid → HCID 15583091, compound

HRID 2412303Notes

Reaction equation

HRID 2412303 reaction equation
[S:1]1[C:5]([NH:6][C:7](=[O:11])[CH2:8][CH2:9][CH3:10])=[CH:4][N:3]=[N:2]1.[H-].[Na+].[H][H].[C:16]1([N:22]=[C:23]=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>O1CCCC1.O>[C:7]([N:6]([C:5]1[S:1][N:2]=[N:3][CH:4]=1)[C:23]([NH:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:24])(=[O:11])[CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 20432881HCID 20432881, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15583091HCID 15583091, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

13.2 g (0.077 mole) butyric acid-N-(1,2,3-thiadiazole-5-yl)-amide were dissolved in 150 ml absolute tetrahydrofuran and reacted with 3.36 g (0.077 mole) of a 55% dispersion of sodium hydride in oil, whereby during the addition the reaction solution through cooling is maintained at 30° C. After about 30 minutes of stirring at room temperature, the evolution of hydrogen is completed. 8.3 ml (0.077 mole) phenylisocyanate is added dropwise within about 5 minutes during which time the reaction temperature increases to 36° C. The reaction mixture is then stirred at room temperature for 1.5 hours whereby a thick crystaline slurry is formed. The reaction mixture is then introduced into a solution of 12.3 ml (0.154 mole) concentrated hydrochloric acid in 300 ml of water. Thereafter the reaction mixture is extracted with 250 ml acetic ester, the organic phase washed with water, dried over magnesium sulfate, filtered and concentrated in vacuum. There were thusly obtained colorless crystals which were digested with 50 ml diisopropylether.

Workup

  1. temperaturethrough cooling
  2. temperatureincreases to 36° C
  3. stirringThe reaction mixture is then stirred at room temperature for 1.5 hours whereby a thick crystaline slurry
  4. customis formed
  5. extractionThereafter the reaction mixture is extracted with 250 ml acetic ester
  6. washthe organic phase washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-4d48a4527a3b4461b532883a37974ec6
Source dataset
uspto-grants-1985_01
Patent number
US04491466

Reaction notes

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