Pyridiniumtribromide → N-(5-(2-Bromoacetyl)thiazol-2-yl)pivalamide

HRID 1942994Notes

Reaction equation

HRID 1942994 reaction equation
[C:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:5]=1)(=[O:3])[CH3:2].[Br-:16].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>Br.CC(O)=O>[Br:16][CH2:2][C:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:5]=1)=[O:3]

Participants

5

Reactant 2

HCID 21124087PyridiniumtribromideHCID 25130143N-(5-acetyl-1,3-thiazol-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 25130826N-(5-(2-Bromoacetyl)thiazol-2-yl)pivalamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

Compound 20z (0.26 g, 1.15 mmol) was dissolved in 33% HBr in HOAc (100 mL), pyridinium tribromide (0.37 g, 1.15 mmol) was added, and the reaction was stirred at room temperature overnight. The reaction mixture was poured onto ice water and the solid was collected by filtration to yield 21z which was in the next step without purification (0.34 g, 97%). 1H NMR (400 MHz, CDCl3): δ 8.12 (s, 1H), 4.27 (s, 2H), 1.36 (s, 9H).

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-5dfe538bf9c244d59702f384e5522fdc
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

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