Pivalic acid → Buthidazolamine

HRID 1253512Notes

Reaction equation

HRID 1253512 reaction equation
[C:1](O)(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[NH:8]([C:10](=[S:12])[NH2:11])[NH2:9].[OH-].[NH4+]>S(=O)(=O)(O)O>[C:2]([C:1]1[S:12][C:10]([NH2:11])=[N:8][N:9]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6417Pivalic acidHCID 14923Ammonium HydroxideHCID 2723789Thiosemicarbazide

Product 1

HCID 170170Buthidazolamine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2 °C

Procedure

To a solution of pivalic acid (85.1 g, 0.833 mol) in concentrated sulfuric acid (280 ml) was slowly added hydrazinecarbothioamide (76.0 g, 0.833 mol) such that the internal temperature was maintained at 0-4° C. After addition was complete, the resulting mixture was heated to 80° C. and monitored by TLC. After the reaction was complete, the resulting yellow solution was cooled to room temperature, poured into ice, and then adjusted the pH to 7 by the addition of aqueous ammonium hydroxide. The resulting precipitate was filtered to obtain 5-tert-butyl-1,3,4-thiadiazol-2-amine which was used directly without purification.

Workup

  1. additionAfter addition
  2. temperaturethe resulting mixture was heated to 80° C.
  3. temperaturethe resulting yellow solution was cooled to room temperature
  4. additionpoured into ice
  5. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-9d57959eed67414fa68a87fdc194c837
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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