Thiosemicarbazide → 5-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

HRID 333918Notes

Reaction equation

HRID 333918 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](Cl)=O)=[CH:5][CH:4]=1.[NH2:13][NH:14][C:15]([NH2:17])=[S:16]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[S:16][C:15]([NH2:17])=[N:14][N:13]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 2723789ThiosemicarbazideHCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 8002315-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(4-methoxyphenyl)acetyl chloride (88a, 3.05 g, 16.5 mmol), and thiosemicarbazide (1.37 g, 15.0 mmol) were heated to 60° C. for 3.0 hours. The reaction mixture was then cooled to room temperature, quenched with water and extracted with ethyl acetate. The organic layer was washed with brine and 50% NaOH(aq), dried over. MgSO4(s), and concentrated under reduced pressure to give 5-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (88b).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine and 50% NaOH(aq)
  5. customdried over
  6. concentrationMgSO4(s), and concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e4f88283c324b40a9e26db55334f919
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

Loading…