p-Aminoacetophenone → 1-(2-Aminobenzo[d]thiazol-6-yl)ethanone

HRID 222641Notes

Reaction equation

HRID 222641 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].[S-:11][C:12]#[N:13].[K+].BrBr.[NH4+].[OH-]>C(O)(=O)C.O>[NH2:13][C:12]1[S:11][C:6]2[CH:5]=[C:4]([C:2](=[O:3])[CH3:1])[CH:9]=[CH:8][C:7]=2[N:10]=1

Participants

7

Reactant 4

HCID 7468p-AminoacetophenoneHCID 14923Ammonium HydroxideHCID 24408BromineHCID 516872Potassium thiocyanate

Product 1

HCID 38473851-(2-Aminobenzo[d]thiazol-6-yl)ethanoneYield 78.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

4-Aminoacetophenone (3.0 g, 22.19 mmol) and potassium thiocyanate (8.87 g, 88.78 mmol) were dissolved in acetic acid (35 mL) and stirred together until they dissolved (˜15-20 min). The solution was then treated with a solution of bromine (1.14 mL, 22.19 mmol) dissolved in acetic acid (15 mL) by slow addition over 20 min. The reaction was then stirred at room temperature for 19 hr and then poured into H2O (100 mL). The solution was then basified to pH=9-10 with NH4OH. The resulting precipitate was collected by vacuum filtration. The solids were then dissolved in hot ethyl acetate and filtered again. The filtrate was concentrated in vacuo to give 3.35 g (76%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.32 (d, J=1.47 Hz, 1H) 7.91 (s, 2H) 7.83 (dd, J=8.46, 1.84 Hz, 1H) 7.37 (d, J=8.46 Hz, 1H) 2.55 (s, 3H). MS m/z (DCI) 193.0 (M+H)+.

Workup

  1. dissolutiondissolved (˜15-20 min)
  2. stirringThe reaction was then stirred at room temperature for 19 hr
  3. filtrationThe resulting precipitate was collected by vacuum filtration
  4. dissolutionThe solids were then dissolved in hot ethyl acetate
  5. filtrationfiltered again
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-71e455e254f641e18860ee501ddae4cf
Source dataset
uspto-grants-2012_06
Patent number
US08207350B2

Reaction notes

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