Hydrochloric Acid → HCID 86735782, compound

HRID 839763Notes

Reaction equation

HRID 839763 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[Cl:7][CH2:8][C:9]([CH2:14]Cl)([CH3:13])[C:10]([Cl:12])=O.P(Cl)(Cl)(Cl)=O.Cl>O1CCOCC1>[CH3:1][NH:2][C:3]1[S:6][C:13]([C:9]([CH2:10][Cl:12])([CH2:8][Cl:7])[CH3:14])=[N:5][N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 2723853N-MethylhydrazinecarbothioamideHCID 43210274301-04-6

Product 1

HCID 86735782HCID 86735782, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of 34 g of 4-methylthiosemicarbazide in 50 ml of dioxane was added 60 g of α,α-bischloromethyl propionyl chloride, then heated to reflux temperature. Carefully 50 g of phosphorus oxychloride was added and heating continued until HCl evolution ceased. After cooling, the supernatant liquid was decanted from the viscous material that had separated, water was added and the mixture taken to a pH of 10 with sodium hydroxide pellets. No precipitate formed. The solution was extracted with chloroform, the extract was shaken with water then with saturated sodium chloride solution and was then dried over Na2 SO4. The chloroform was removed at reduced pressure and the residue crystallized with a mixture of methylene chloride-petroleum ether to give 27.8 g, m.p. 105°-107° (36%). An analytical sample, m.p. 108°-109°, was prepared from methylene chloride-petroleum ether.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature
  3. temperatureheating
  4. temperatureAfter cooling
  5. customthe supernatant liquid was decanted from the viscous material that
  6. customhad separated
  7. additionwater was added
  8. customNo precipitate formed
  9. extractionThe solution was extracted with chloroform
  10. dry with materialwith saturated sodium chloride solution and was then dried over Na2 SO4
  11. customThe chloroform was removed at reduced pressure
  12. customthe residue crystallized with a mixture of methylene chloride-petroleum ether
  13. customto give 27.8 g, m.p. 105°-107° (36%)

Sources & evidence

ORD record
ord-50fd7413e652443795f8ce8825b8e4f2
Source dataset
uspto-grants-1978_06
Patent number
US04097264

Reaction notes

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