Butylamine → N-Butyl-3-methyl-1,2,4-thiadiazol-5-amine

HRID 1862806Notes

Reaction equation

HRID 1862806 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([CH3:7])[N:3]=1.[CH2:8]([NH2:12])[CH2:9][CH2:10][CH3:11]>C(O)C>[CH2:8]([NH:12][C:2]1[S:6][N:5]=[C:4]([CH3:7])[N:3]=1)[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 129191595-Chloro-3-methyl-1,2,4-thiadiazole

Product 1

HCID 20393662N-Butyl-3-methyl-1,2,4-thiadiazol-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-3-methyl-1,2,4-thiadiazole (27 g, 0.20 mol) was dissolved in 200 ml ethanol and, under cooling in an ice bath, added to an ethanolic solution of butylamine (44 g, 0.60 mol), stirred at room temperature overnight and evaporated to small bulk. Upon addition of ether a white precipitate of butylamine hydrochloride formed which was filtered off. The yellow filtrate was washed with water, dried over magnesium sulphate, filtered and evaporated to dryness to yield a yellow oil which was distilled under vacuum to give 5-butylamino-3-methyl-1,2,4-thiadiazole as a pale yellow liquid. Yield 29.9 g, (87.2%), b.p. 101°-102° C./0.14 mmHg.

Workup

  1. temperatureunder cooling in an ice bath
  2. customevaporated to small bulk
  3. additionUpon addition of ether a white precipitate of butylamine hydrochloride
  4. customformed which
  5. filtrationwas filtered off
  6. washThe yellow filtrate was washed with water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customto yield a yellow oil which
  11. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-433ab213b2df4363a0e5acc0e66b0784
Source dataset
uspto-grants-1979_09
Patent number
US04166818

Reaction notes

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