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

HRID 2083558Notes

Reaction equation

HRID 2083558 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[C:7](O)(=O)[C:8]([CH3:11])([CH3:10])[CH3:9].P(Cl)(Cl)(Cl)=O.Cl>O1CCOCC1>[C:8]([C:11]1[S:6][C:3]([NH:2][CH3:1])=[N:4][N:5]=1)([CH3:10])([CH3:9])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6417Pivalic acidHCID 24813Phosphorus oxychlorideHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 1708665-(1,1-Dimethylethyl)-N-methyl-1,3,4-thiadiazol-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 91.6 g of 4-methylthiosemicarbazide and 102.3 g of pivalic acid in 400 ml of dioxane at 90° is added slowly 160.5 g of phosphorus oxychloride at such a rate that the reaction temperature is maintained at 85°-90° C. without external heating. When the addition is complete, the mixture is heated at 85°-90° C until HCl evolution ceases (several hours), is cooled and the supernatant liquid decanted from the solid mass in the flask. The mass is broken up, slurried with 700 ml of water and made basic (pH 8-9) by the slow addition of sodium hydroxide pellets. The resulting precipitate is filtered, washed with water, air dried and recrystallized from hexane to give 119.4 g (80% yield) of 2-tert.butyl-5-methylamino-1,3,4-thiadiazole, m.p. 79°-81°.

Workup

  1. temperatureis maintained at 85°-90° C. without external heating
  2. additionWhen the addition
  3. temperatureis cooled
  4. customthe supernatant liquid decanted from the solid mass in the flask
  5. additionby the slow addition of sodium hydroxide pellets
  6. filtrationThe resulting precipitate is filtered
  7. washwashed with water, air
  8. customdried
  9. customrecrystallized from hexane

Sources & evidence

ORD record
ord-bb3764c945f840fabf498352cf848579
Source dataset
uspto-grants-1978_04
Patent number
US04086077

Reaction notes

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