Water → 5-Methyl-N-(propan-2-yl)-1,3,4-thiadiazol-2-amine

HRID 236900Notes

Reaction equation

HRID 236900 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[BH4-].[Na+].O.[CH3:11][CH:12](O)[CH3:13]>CC(C)=O>[CH3:7][C:4]1[S:3][C:2]([NH:1][CH:12]([CH3:13])[CH3:11])=[N:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 4311764Sodium borohydride

Product 1

HCID 5446705-Methyl-N-(propan-2-yl)-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-5-methyl-1,3,4-thiadiazole (23 g, 0.2 mole) in IPA (700 ml) and acetone (100 ml) was treated with sodium borohydride (20 g) in portions with stirring and cooling. The reaction mixture was then stirred and heated to reflux for 31/2 hours. The solution was then poured into water (3 L) and extracted with ether (× 3). The ethereal solution was dried, filtered and evaporated to give the title compound as a cream solid. m.p. 145° C.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was then stirred
  3. temperatureheated
  4. temperatureto reflux for 31/2 hours
  5. extractionextracted with ether (× 3)
  6. customThe ethereal solution was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-325450a20bdc482b8daf12aee7195583
Source dataset
uspto-grants-1979_06
Patent number
US04158659

Reaction notes

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