Methylhydrazine → 3-Amino-1-methyl-5-methylthio-1,2,4-triazole

HRID 904986Notes

Reaction equation

HRID 904986 reaction equation
[CH3:1][NH:2]N.[C:4]([N:6]=[C:7](SC)[S:8][CH3:9])#[N:5].C(#[N:14])C>>[NH2:14][C:4]1[N:6]=[C:7]([S:8][CH3:9])[N:2]([CH3:1])[N:5]=1

Participants

4

Reactant 3

HCID 6061MethylhydrazineHCID 6342AcetonitrileHCID 66289Dimethyl N-cyanodithioiminocarbonate

Product 1

HCID 5228203-Amino-1-methyl-5-methylthio-1,2,4-triazole

Procedure

At 0°, 6.5 grams of methyl hydrazine was added dropwise to a stirred suspension of 20.0 grams (0.137 mole) dimethyl cyanodithioimidocarbonate in 35 ml of acetonitrile. A yellow solution immediately formed after the addition followed by precipitation of a white solid. The ice bath was removed, and upon warming to room temperature a yellow solution formed which was stirred at room temperature overnight. After stirring overnight, a solid precipitated which was filtered, washed with cold acetonitrile, followed by 1-chlorobutane, yield 8.5 grams, m.p. 104°-109°. The literature [Journal of Organic Chemistry, 39, 1522 (1974)] reported a similar melting point of 103°-106° for the title compound, however, a different isomeric structure was assigned to the compound (5-amino-1-methyl-3-methylthio-1H-1,2,4-triazole). The assignment of 3-amino-1-methyl-5-methylthio-1H-1,2,4-triazole as the correct structure was verified by X-ray crystal structure analysis.

Workup

  1. customA yellow solution immediately formed
  2. additionafter the addition
  3. customfollowed by precipitation of a white solid
  4. customThe ice bath was removed
  5. customformed which
  6. stirringAfter stirring overnight
  7. customa solid precipitated which
  8. filtrationwas filtered
  9. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-e3df1706520d4734bd87d32f3dc98233
Source dataset
uspto-grants-1983_12
Patent number
US04421550

Reaction notes

Loading…