Ammonia → 5-(2-Chloroethyl)-1,3,4-thiadiazol-2-amine

HRID 908183Notes

Reaction equation

HRID 908183 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[Cl:6][CH2:7][CH2:8][C:9](O)=O.O.N>S(=O)(=O)(O)O>[Cl:6][CH2:7][CH2:8][C:9]1[S:4][C:3]([NH2:5])=[N:2][N:1]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 78993-Chloropropionic acidHCID 2723789Thiosemicarbazide

Product 1

HCID 150317075-(2-Chloroethyl)-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
75 °C

Procedure

Thiosemicarbazide (10 g, 111 mmol) is added in portions to a solution of 3-chloropropionic acid (10 g, 92 mmol) in concentrated sulfuric acid. The mixture is heated with stirring at 75° C. for 1 hour. After cooling to room temperature the reaction mixture id added slowly to water and the resulting solution is brought to pH 7 by addition of aqueous ammonia solution. The titled product precipitates as a yellow solid which is removed by filtration and dried.

Workup

  1. temperatureThe mixture is heated
  2. temperatureAfter cooling to room temperature the reaction mixture id
  3. customThe titled product precipitates as a yellow solid which
  4. customis removed by filtration
  5. customdried

Sources & evidence

ORD record
ord-900e21fc089548998abaeb12ea741dbe
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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