1,3,4-Thiadiazol-2-amine → HCID 19361559, compound

HRID 376250Notes

Reaction equation

HRID 376250 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[NH2:9][C:10]1[S:11][CH:12]=[N:13][N:14]=1>C(O)C>[ClH:1].[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][N:14]1[N:13]=[CH:12][S:11][C:10]1=[NH:9]

Participants

4

Reactant 2

HCID 199091,3,4-Thiadiazol-2-amineHCID 23393Picolyl chloride

Product 1

HCID 19361559HCID 19361559, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloromethylpyridine (1.75 g, 0.0137 M) and 2-amino-1,3,4-thiadiazole (1.09 g, 0.0108 M) in 20 mL ethyl alcohol was refluxed for 20 hours. The reaction mixture was cooled to room temperature and filtered. The precipitate was washed with ethyl acetate and dried to yield 0.680 g of the title compound. MP=187-189° C. 1H-NMR (DMSO-d6) δ 10.6 (br s, 1H), 9.0 (s, 1H), 8.5 (d, 1H), 7.9 (m, 1H), 7.48 (d, 1H), 7.38 (m, 1H), 5.7 (s, 2H). 13C-NMR (DMSO-d6) δ 167.7, 153.0, 149.3, 145.0, 137.4, 123.4, 122.4, 54.0. Mass spectrum: m/e=193 (p+1).

Workup

  1. temperaturewas refluxed for 20 hours
  2. filtrationfiltered
  3. washThe precipitate was washed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-097f220bf8a0409b89d27c6e01dcc79e
Source dataset
uspto-grants-2000_02
Patent number
US06020335

Reaction notes

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