Phosgene → HCID 20355010, compound

HRID 1606087Notes

Reaction equation

HRID 1606087 reaction equation
C(SC1N=CNN=1)C.C(Cl)(Cl)=O.[C:13](N1C=NC(SCC)=N1)([N:15]1[CH:19]=[N:18][C:17]([S:20][CH2:21][CH3:22])=[N:16]1)=[O:14].[CH2:31]([NH:34][CH2:35][CH2:36][CH3:37])[CH2:32][CH3:33]>O1CCCC1.N1C=CC=CC=1>[CH2:31]([N:34]([CH2:35][CH2:36][CH3:37])[C:13]([N:15]1[CH:19]=[N:18][C:17]([S:20][CH2:21][CH3:22])=[N:16]1)=[O:14])[CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8902DipropylamineHCID 20355007HCID 20355007, compoundHCID 178477350HCID 178477350, compound

Product 1

HCID 20355010HCID 20355010, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 51.6 g. 3-ethylthio-1,2,4-triazole and 31.6 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, 0.5 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 1,1'-carbonylbis(3-ethylthio-1,2,4-triazole) was added dropwise with stirring a solution of 20.2 g. dipropylamine in 50 ml. dry tetrahydrofuran. The mixture was stirred for a further period of 0.5 hour, and was then evaporated under reduced pressure to remove solvent. The residual oil was dissolved in methylene dichloride and 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° - 132°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. stirringwith stirring a solution of 20.2 g
  7. stirringThe mixture was stirred for a further period of 0.5 hour
  8. customwas then evaporated under reduced pressure
  9. customto remove solvent
  10. dissolutionThe residual oil was dissolved in methylene dichloride
  11. washthe resulting solution was washed successively with 0.5N sodium hydroxide solution, water, and finally 0.5N hydrochloric acid
  12. distillationThe washed solution was distilled under reduced pressure

Sources & evidence

ORD record
ord-d967af58e2f74fdd96d3929e8e0c9947
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

Loading…