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

HRID 127127

Reaction equation

HRID 127127 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([S:10](Cl)(=[O:12])=[O:11])=[N:8][N:9]=1)(=[O:3])[CH3:2].Cl.[CH3:15][NH:16][CH3:17]>>[C:1]([NH:4][C:5]1[S:6][C:7]([S:10]([N:16]([CH3:17])[CH3:15])(=[O:12])=[O:11])=[N:8][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 128944515-(Acetylamino)-1,3,4-thiadiazole-2-sulfonyl chloride

Product 1

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

Conditions

Temperature
20 °C

Procedure

A 40% aqueous solution of dimethylamine (400 ml) was charged into a glass reaction vessel fitted with a mechanical stirrer and thermometer. The solution was cooled to 20° C. and stirred while 2-acetamido-5-chlorosulfonyl-1,3,4-thiadiazole (250 grams) was slowly added. Ther temperature of the reaction mixture was kept between 0° and 20° C. during this addition. Stirring was then continued at room temperature for a period of about 2 hours. The reaction mixture was then treated with 6N hydrochloric acid. Solids were filtered out, water washed and air dried to yield the desired product 2-acetamido-5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazole.

Workup

  1. customfitted with a mechanical stirrer
  2. additionwas slowly added
  3. additionTher temperature of the reaction mixture was kept between 0° and 20° C. during this addition
  4. filtrationSolids were filtered out
  5. washwater washed
  6. customair dried

Sources & evidence

ORD record
ord-a23b66c6946740269aeea64134b4abe4
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Linked notes

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