4-Bromophenacyl bromide → HCID 19209621, compound

HRID 643649Notes

Reaction equation

HRID 643649 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)=O.C([O-])(O)=O.[Na+]>CCO>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]3[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=4)[N:1]=[C:2]3[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 156302-Amino-6-methoxybenzothiazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 19209621HCID 19209621, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the minimum volume of EtOH was dissolved the commercially available 2-amino-6-methoxybenzothiazole (2 mmol), then 2,4′-dibromoacetophenone (2 mmol) was added and the resulting mixture was refluxed for 5 h before addition of NaHCO3 (3 mmol). After 2 h more of reflux, the precipitate was filtered off, washed with a mixture 1/1 AcOEt/hexane and dried in vacuum and then used in the next step, optionally, without further purification. The result was a white solid as a 54% yield.

Workup

  1. temperatureAfter 2 h more of reflux
  2. filtrationthe precipitate was filtered off
  3. washwashed with a mixture 1/1 AcOEt/hexane
  4. customdried in vacuum
  5. customoptionally, without further purification

Sources & evidence

ORD record
ord-090bc07049ff465dbe4b600917496ed9
Source dataset
uspto-grants-2010_04
Patent number
US07700616B2

Reaction notes

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