N-bromobutanimide → N-(5-bromothiazol-4-yl)acetamide

HRID 1051422Notes

Reaction equation

HRID 1051422 reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:17])[CH3:16])[N:11]=[CH:10]1>CC(O)=O.C1COCC1>[Br:1][C:13]1[S:9][CH:10]=[N:11][C:12]=1[NH:14][C:15](=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 202940374-Acetamidothiazole

Product 1

HCID 86715556N-(5-bromothiazol-4-yl)acetamideYield 54.3%

Reagents, catalysts & solvents 1

HCID 23444217Acetic acid tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

1-Bromopyrrolidine-2,5-dione (0.48 g, 2.67 mmol) was added to the solution of N-(thiazol-4-yl)acetamide (0.38 g, 2.67 mmol) in AcOH/THF (10 mL/10 mL). The mixture was heated to 25° C. for 2 h. The solvent was removed and the solution was adjusted to pH˜9 with 2 N NaOH solution. It was extracted with EA (3×50 mL), the combined organic phase was washed with brine, dried with Na2SO4 and concentrated to give the title compound (1.32 g, 1.45 mmol, 54.2%) as light yellow solid.

Workup

  1. customThe solvent was removed
  2. extractionIt was extracted with EA (3×50 mL)
  3. washthe combined organic phase was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b6376ab244d74ea6a62023c32bb595e4
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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