Hydrochloric Acid → 2-amino-5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazole

HRID 127128Notes

Reaction equation

HRID 127128 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[N:8][N:9]=1)(=O)C.Cl>>[NH2:4][C:5]1[S:6][C:7]([S:10]([N:13]([CH3:15])[CH3:14])(=[O:11])=[O:12])=[N:8][N:9]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 128944522-acetamido-5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazole

Product 1

HCID 128944532-amino-5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazole

Procedure

2-Acetamido-5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazole (250 grams) and concentrated hydrochloric acid (1 L) were charged into a glass reaction vessel fitted with a mechanical stirrer, reflux condenser and thermometer. This mixture was refluxed for a period of about 2 hours. It was then cooled to room temperature, filtered and the solvent stripped from the filtrate using a rotary evaporator. The solid residue was washed with 10% aqueous sodium carbonate (200 ml), air dried, then crystallized from isopropanol. These crystals were the desired product 2-amino-5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazole and having a melting point of 188°-190° C.

Workup

  1. customfitted with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThis mixture was refluxed for a period of about 2 hours
  4. filtrationfiltered
  5. customa rotary evaporator
  6. washThe solid residue was washed with 10% aqueous sodium carbonate (200 ml), air
  7. customdried
  8. customcrystallized from isopropanol

Sources & evidence

ORD record
ord-ae45236eeb9d4e91821c4aa34c037b6f
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Reaction notes

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