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

HRID 2371369Notes

Reaction equation

HRID 2371369 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 Example 1A) in 150 ml of lN 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 lN 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.

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 lN hydrochloric acid
  7. filtrationThe product was collected by filtration
  8. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-e1cc74783a9f4a7ea3951a4e736763a3
Source dataset
uspto-grants-1992_03
Patent number
US05093324

Reaction notes

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