3-Nitrobenzenesulfonyl chloride → HCID 19203800, compound

HRID 2379337Notes

Reaction equation

HRID 2379337 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[N+:7]([C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].[OH-].[Na+]>N1C=CC=CC=1>[S:3]1[CH:4]=[N:5][N:6]=[C:2]1[NH:1][S:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1)(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 199091,3,4-Thiadiazol-2-amine

Product 1

HCID 19203800HCID 19203800, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred suspension of 2-amino-1,3,4-thiadiazole (1.5 g, 15 mmol) in anhydrous pyridine (6 ml) at 0° C., under nitrogen, was added 3-nitrobenzenesulphonyl chloride (3.5 g, 16 mmol) portionwise. The mixture turned yellow and set solid. The mixture was then heated at 120° C. for 1 h before aqueous sodium hydroxide (20% (w/w), 3.3 ml) was added cautiously. Heating was continued for a further 15 min then the solution allowed to cool to ambient temperature. The mixture was evaporated in vacuo and the residue evaporated with water (2×50 ml) followed by toluene (2×50 ml). The residue was then taken up in water and the resultant brown solid collected by filtration. This was then recrystallised from glacial acetic acid. The title compound (1.4 g, 37%) was isolated as a yellow solid, which contained one mole of acetic acid. mp 189°-192° C. 1H NMR (250 MHz, D6 -DMSO) δ 7.88 (1H, dd, J=8 and 8 Hz), 8.23 (1H, dd, J=8 and 1 Hz), 8.45 (2H, m), 8.83 (1H, s).

Workup

  1. additionwas added cautiously
  2. temperatureHeating
  3. customThe mixture was evaporated in vacuo
  4. customthe residue evaporated with water (2×50 ml)
  5. filtrationthe resultant brown solid collected by filtration
  6. customThis was then recrystallised from glacial acetic acid

Sources & evidence

ORD record
ord-6bd8ff05f50243b189cd279d084d6630
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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