Phenacyl bromide → 25752-18-5

HRID 904610Notes

Reaction equation

HRID 904610 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O>C(O)C>[C:11]1([C:9]2[N:1]=[C:2]3[N:6]([CH:8]=2)[N:5]=[CH:4][S:3]3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 199091,3,4-Thiadiazol-2-amine

Product 1

HCID 85354725752-18-5

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.1 g. of 2-amino-1,3,4-thiadiazole are dissolved in 160 ml. of ethanol, 19.9 g. of α-bromoacetophenone is added and the solution is heated and stirred at reflux for 1 hour. After cooling, the solid is filtered off and dissolved in 750 ml. of water and 40 ml. of 48% hydrobromic acid. This solution is heated at reflux for 1 hour, neutralized by addition of solid ammonium acetate and refluxed 1/2 hour longer. After cooling, the product is collected on a filter, washed with water and dried. The yield of product is 13 g. melting at 127°-130° C. It has the formula: ##STR15##

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe solid is filtered off
  5. dissolutiondissolved in 750 ml
  6. temperatureThis solution is heated
  7. temperatureat reflux for 1 hour
  8. additionneutralized by addition of solid ammonium acetate
  9. temperaturerefluxed 1/2 hour longer
  10. temperatureAfter cooling
  11. customthe product is collected on a filter
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-420c48a2e5f94da09317aa84c11732aa
Source dataset
uspto-grants-1983_12
Patent number
US04419289

Reaction notes

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