Phosgene → HCID 20355010, compound

HRID 1606085Notes

Reaction equation

HRID 1606085 reaction equation
C(SC1N=CNN=1)C.C(Cl)(Cl)=O.[CH2:13]([S:15][C:16]1[N:20]=[CH:19][N:18]([C:21](Cl)=[O:22])[N:17]=1)[CH3:14].[CH2:24]([NH:27][CH2:28][CH2:29][CH3:30])[CH2:25][CH3:26]>O1CCCC1.N1C=CC=CC=1>[CH2:24]([N:27]([CH2:28][CH2:29][CH3:30])[C:21]([N:18]1[CH:19]=[N:20][C:16]([S:15][CH2:13][CH3:14])=[N:17]1)=[O:22])[CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8902DipropylamineHCID 20355045HCID 20355045, compoundHCID 178477350HCID 178477350, compound

Product 1

HCID 20355010HCID 20355010, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 25.8 g. 3-ethylthio-1,2,4-triazole and 15.8 g. dry pyridine in 100 ml. dry tetrahydrofuran was added dropwise to 200 ml. of a 10% w/v solution of phosgene in dry tetrahydrofuran (20 g. phosgene, 1 molecular proportion), with stirring and cooling to maintain the reaction temperature at 25° - 30°C. The mixture was stirred at 25° - 30°C. for a further period of 0.5 hour, and was then filtered to remove pyridine hydrochloride formed in the reaction. To the resulting solution of 3-ethylthio-1,2,4-triazole-1-carbonyl chloride was added dropwise a solution of 20.2 g. dipropylamine and 15.8 g. dry pyridine in 50 ml. dry tetrahydrofuran, with stirring and cooling to maintain the reaction temperature at 25° - 30°C. The mixture was stirred at 25° - 30°C. for a further period of 0.5 hour, and was then filtered to remove pyridine hydrochloride formed in the reaction. The filtrate was evaporated under reduced pressure to remove solvent and the residual oil was dissolved in methylene dichloride. The resulting solution was washed successively with 0.5N sodium hydroxide solution, water, and finally 0.5N hydrochloric acid. The washed solution was distilled under reduced pressure to give 1-dipropylcarbamoyl-3-ethylthio-1,2,4-triazole, b.p. 130°C./0.5 mm. Elemental analysis satisfactory.

Workup

  1. temperaturecooling
  2. temperatureto maintain the reaction temperature at 25° - 30°C
  3. filtrationwas then filtered
  4. customto remove pyridine hydrochloride
  5. customformed in the reaction
  6. temperaturecooling
  7. temperatureto maintain the reaction temperature at 25° - 30°C
  8. stirringThe mixture was stirred at 25° - 30°C. for a further period of 0.5 hour
  9. filtrationwas then filtered
  10. customto remove pyridine hydrochloride
  11. customformed in the reaction
  12. customThe filtrate was evaporated under reduced pressure
  13. customto remove solvent
  14. dissolutionthe residual oil was dissolved in methylene dichloride
  15. washThe resulting solution was washed successively with 0.5N sodium hydroxide solution, water, and finally 0.5N hydrochloric acid
  16. distillationThe washed solution was distilled under reduced pressure

Sources & evidence

ORD record
ord-bd795d504bc3455d9d41b231b7d2a1a6
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

Loading…