Hydrochloric Acid → 5-(1-Chloro-2-methylpropan-2-yl)-N-methyl-1,3,4-thiadiazol-2-amine

HRID 839762Notes

Reaction equation

HRID 839762 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[Cl:7][CH2:8][C:9]([CH3:14])([CH3:13])[C:10](O)=O.P(Cl)(Cl)(Cl)=O.Cl>O1CCOCC1>[CH3:1][NH:2][C:3]1[S:6][C:10]([C:9]([CH3:14])([CH3:13])[CH2:8][Cl:7])=[N:5][N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 83542beta-Chloropivalic acidHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 127696565-(1-Chloro-2-methylpropan-2-yl)-N-methyl-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a well stirred suspension of 125 g of 4-methylthiosemicarbazide and 165 g of β-chloropivalic acid in 500 ml of dioxane was added 186 g of phosphorus oxychloride at a rate which maintained the temperature below 60°. The reaction mixture was then heated at reflux until HCl evolution ceased (about 4 hrs). After cooling, the supernatant liquid was decanted from the plastic mass and 500 ml of water was added. With cooling, sodium hydroxide pellets were added until a pH of 10 was maintained. The resulting precipitate was collected, washed with water and air dried giving 216 g m.p. 91°-93°, (87%). Recrystallization from methylene chloride-ether gave the analytical sample, m.p. 93°-95°.

Workup

  1. temperaturemaintained the temperature below 60°
  2. temperatureThe reaction mixture was then heated
  3. custom(about 4 hrs)
  4. temperatureAfter cooling
  5. customthe supernatant liquid was decanted from the plastic mass and 500 ml of water
  6. additionwas added
  7. temperatureWith cooling
  8. additionsodium hydroxide pellets were added until a pH of 10
  9. temperaturewas maintained
  10. customThe resulting precipitate was collected
  11. washwashed with water and air
  12. customdried
  13. customgiving 216 g m.p. 91°-93°, (87%)
  14. customRecrystallization from methylene chloride-ether
  15. customgave the analytical sample, m.p. 93°-95°

Sources & evidence

ORD record
ord-4c649baa67314fc29bb4bbcea935e42b
Source dataset
uspto-grants-1978_06
Patent number
US04097264

Reaction notes

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