Hydrogen Bromide → 2-Bromo-5-nitrothiazole

HRID 1422030Notes

Reaction equation

HRID 1422030 reaction equation
N[C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.N([O-])=O.[Na+].[BrH:14]>O.CCCCCO>[Br:14][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 84862-Amino-5-NitrothiazoleHCID 23668193Sodium Nitrite

Product 1

HCID 182112-Bromo-5-nitrothiazoleYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 62761-PentanolSolvent

Conditions

Temperature
-10 °C

Procedure

To 72.5 g of 2-amino-5-nitrothiazole in 300 mL of 48% hydrobromic acid and 200 mL of water stirred and cooled to about -10° C. was slowly added, in portions, 51.8 g of sodium nitrite dissolved in 80 mL of water from one addition funnel and 250 mL of n-amyl alcohol from a second addition funnel. The addition of both solutions required about 3 hours. The cooling bath was removed and the mixture allowed to warm to about 15° C. overnight and then stirred at room temperature for 2 hours. The solid was collected by vacuum filtration and steam distilled to give 67 g of crude product. The crude product was recrystallized from hot ethanol to give 61 g (60% yield) of the 2-bromo-5-nitrothiazole as a yellow solid.

Workup

  1. additionThe addition of both solutions required about 3 hours
  2. customThe cooling bath was removed
  3. temperatureto warm to about 15° C. overnight
  4. filtrationThe solid was collected by vacuum filtration and steam
  5. distillationdistilled
  6. customto give 67 g of crude product
  7. customThe crude product was recrystallized from hot ethanol

Sources & evidence

ORD record
ord-c9920d887d3a4d1dadfbf42762eb7fe3
Source dataset
uspto-grants-2000_06
Patent number
US06080772

Reaction notes

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