Methylamine → 5-amino-N-methyl-1,3,4-thiadiazole-2-sulfonamide

HRID 731496Notes

Reaction equation

HRID 731496 reaction equation
[CH3:1][NH2:2].C([NH:6][C:7]1[S:11][C:10]([S:12](Cl)(=[O:14])=[O:13])=[N:9][N:8]=1)(=O)C>C1COCC1>[CH3:1][NH:2][S:12]([C:10]1[S:11][C:7]([NH2:6])=[N:8][N:9]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 128944515-(Acetylamino)-1,3,4-thiadiazole-2-sulfonyl chloride

Product 1

HCID 674836825-amino-N-methyl-1,3,4-thiadiazole-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (2M in THF, 40 mmol) was added to a suspension of 5-acetylamino-1,3,4-thiadiazole-2-sulfonyl chloride (10 mmol) (prepared as described in Bioorg. Med. Chem. 5, 515, 1997) in THF (10 mL) at −20° C. The mixture was stirred at room temperature over night and evaporated to dryness. The crude methylsulfonamide was suspended in EtOH (15 mL) and added 4N HCl in dioxane (15 mL) and heated for 4 h at 80° C. and then cooled to room temperature and evaporated to dryness to give crude 5-amino-1,3,4-thiadiazole-2-sulfonic acid methylamide.

Workup

  1. customevaporated to dryness
  2. additionadded 4N HCl in dioxane (15 mL)
  3. temperatureheated for 4 h at 80° C.
  4. temperaturecooled to room temperature
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-182dba6a50ef45dc97d03ccfdac3c922
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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