Benzo(d)thiazol-2-amine → HCID 12926121, compound

HRID 615155Notes

Reaction equation

HRID 615155 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH:12]([CH3:21])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O>C(#N)C>[CH3:21][C:12]1[N:6]2[C:2]([S:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=32)=[N:1][C:13]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 164522-Bromopropiophenone

Product 1

HCID 12926121HCID 12926121, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 50 ml of acetonitrile were added 10 g of 2-aminobenzothiazole and 7 g of α-bromopropiophenone and the mixture was refluxed for 3 days. After cooling the reaction mixture, the precipitated hydrobromide of 2-aminobenzothiazole was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in 50 ml of chloroform and then 100 ml of ethyl acetate was added to the solution. The supernatant formed was recovered and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography and then the product was eluted using chloroform as the eluant to provide 1.5 g of 3-methyl-2-phenylimidazo[2,1-b]benzothiazole.

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. temperatureAfter cooling the reaction mixture
  3. filtrationthe precipitated hydrobromide of 2-aminobenzothiazole was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 50 ml of chloroform
  6. addition100 ml of ethyl acetate was added to the solution
  7. customThe supernatant formed
  8. customwas recovered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue obtained
  11. washthe product was eluted

Sources & evidence

ORD record
ord-3ae555c23b1f48248a518bb5b95784f1
Source dataset
uspto-grants-1985_02
Patent number
US04497817

Reaction notes

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