Dimethylformamide → HCID 20159873, compound

HRID 256479Notes

Reaction equation

HRID 256479 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 ice-water 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. filtrationthe precipitate is filtered off with suction
  2. customAfter drying
  3. additionafter the addition of ether
  4. customrecrystallized
  5. temperatureThe crude 2-bromo-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole is then heated
  6. temperatureto reflux for 2 hours in 250 ml of ethanol with 25 ml of 30% strength methylamine solution
  7. temperatureAfter cooling down
  8. customprecipitation
  9. additionis by addition of 200 ml of water
  10. filtrationthe precipitate is filtered off with suction
  11. customrecrystallized from chloroform/ether

Sources & evidence

ORD record
ord-81f38c374310427fb9b11213527887f3
Source dataset
uspto-grants-1987_10
Patent number
US04703125

Reaction notes

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