Bromine → 5-Bromo-4-isopropylthiazol-2-amine

HRID 506624Notes

Reaction equation

HRID 506624 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([NH2:9])[S:7][CH:8]=1)([CH3:3])[CH3:2].[Br:10]Br.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:10][C:8]1[S:7][C:6]([NH2:9])=[N:5][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 70640774-(Propan-2-yl)-1,3-thiazol-2-amine

Product 1

HCID 534881395-Bromo-4-isopropylthiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4-isopropyl-thiazol-2-ylamine (2.0 g, 14 mmol) in 30 mL CHCl3 was added dropwise to a stirring solution of bromine ((2.697 g, 17 mmol) in 15 mL CHCl3. The reaction mixture was stirred for 60 hours at room temperature. The reaction mixture was poured into saturated aqueous NaHCO3, and extracted with methylene chloride. The combined organic extracts were washed with saturated aqueous NaHCO3 and brine, dried (MgSO4), filtered and concentrated under reduced pressure to give 2.05 g of 5-bromo-4-isopropyl-thiazol-2-ylamine as an oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ce79d5f437e49689190bcb2f29b2e24
Source dataset
uspto-grants-2010_08
Patent number
US07786110B2

Reaction notes

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