Ethyl [(1,3,4-thiadiazol-2-ylamino)thioxomethyl]carbamate → 1,3,4-Thiadiazol-2-yl-thiourea

HRID 1762852Notes

Reaction equation

HRID 1762852 reaction equation
[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[NH:6][C:7]([NH:9]C(=O)OCC)=[S:8]>[OH-].[Na+]>[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[NH:6][C:7]([NH2:9])=[S:8]

Participants

3

Reactant 1

HCID 1504157Ethyl [(1,3,4-thiadiazol-2-ylamino)thioxomethyl]carbamate

Product 1

HCID 28069741,3,4-Thiadiazol-2-yl-thioureaYield 72.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 10 g of [(1,3,4-thiadiazol-2-ylamino)thioxomethyl]carbamic acid, ethyl ester (from Preparation 1) in 150 ml of 1N sodium hydroxide was heated at reflux for ninety minutes. The solution was cooled and concentrated by evaporation under reduced pressure. The precipitated solid was collected by filtration and dissolved in 20 ml of water. The aqueous solution was acidified by addition of 200 ml of 1N hydrochloric acid. The product was collected by filtration and recrystallized from N,N-dimethylformamide to give 5 g of 1,3,4-thiadiazol-2-ylthiourea. m.p. 253° C. p Analysis calc. for C3H4N4S2 :

Workup

  1. temperatureat reflux for ninety minutes
  2. temperatureThe solution was cooled
  3. concentrationconcentrated by evaporation under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration
  5. dissolutiondissolved in 20 ml of water
  6. additionThe aqueous solution was acidified by addition of 200 ml of 1N hydrochloric acid
  7. filtrationThe product was collected by filtration
  8. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-0fa00639f1d84c759d6bac5037c3de07
Source dataset
uspto-grants-1989_05
Patent number
US04835168

Reaction notes

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