Dimethylformamide → HCID 20159873, compound

HRID 247570Notes

Reaction equation

HRID 247570 reaction equation
Br[C:2]1[S:3][C:4]([NH2:7])=[N:5][N:6]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.[CH3:18][N:19](C)C=O>>[CH3:18][NH:19][C:2]1[S:3][C:4]2=[N:7][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][N:5]2[N:6]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 6259Phenacyl bromideHCID 36508832-Amino-5-bromo-1,3,4-thiadiazole

Product 1

HCID 20159873HCID 20159873, compound

Procedure

18.0 g of 2-bromo-5-amino-1,3,4-thiadiazole (0.1 mol) and 20.0 g of ω-bromoacetophenone (0.1 mol) in 250 ml of dimethylformamide are heated to 100° C. for 4.5 hours. After cooling down to room temperature, 100 ml of icewater are added and the precipitate is filtered off with suction. After drying, it is taken up in chloroform and, after the addition of ether, recrystallized. The crude 2-bromo-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole is then heated to reflux for 2 hours in 250 ml of ethanol with 25 ml of 30% strength methylamine solution. After cooling down, precipitation is by addition of 200 ml of water, the precipitate is filtered off with suction and recrystallized from chloroform/ether.

Workup

  1. addition100 ml of icewater are added
  2. filtrationthe precipitate is filtered off with suction
  3. customAfter drying
  4. additionafter the addition of ether
  5. customrecrystallized
  6. temperatureThe crude 2-bromo-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole is then heated
  7. temperatureto reflux for 2 hours in 250 ml of ethanol with 25 ml of 30% strength methylamine solution
  8. temperatureAfter cooling down
  9. customprecipitation
  10. additionis by addition of 200 ml of water
  11. filtrationthe precipitate is filtered off with suction
  12. customrecrystallized from chloroform/ether

Sources & evidence

ORD record
ord-880c5c5d9abf4bc9a28c7c7b1aa56962
Source dataset
uspto-grants-1987_11
Patent number
US04709031

Reaction notes

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