Hydrochloric Acid → (6-Bromo-pyridin-2-YL)thiourea

HRID 49139Notes

Reaction equation

HRID 49139 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]([NH:11]C(=O)C2C=CC=CC=2)=[S:10])[N:3]=1.[OH-].[Na+].Cl.C(=O)(O)[O-].[K+]>>[Br:1][C:2]1[N:3]=[C:4]([NH:8][C:9]([NH2:11])=[S:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516893Potassium BicarbonateHCID 206355402-Bromo-6-benzoylthioureidopyridine

Product 1

HCID 22170428(6-Bromo-pyridin-2-YL)thioureaYield 94%

Procedure

A suspension of 2-bromo-6-benzoylthioureidopyridine (4.99 g, 14.84 mmol) in 10% aqueous sodium hydroxide solution (10.4 mL, 26 mmol) was stirred at rt. for 10 min and then under reflux for an additional 10 min. The mixture was cooled to 0° C. and acidified with 1 N aqueous HCl solution to pH 4.0 and then adjusted to pH 8.5 with satd. aqueous potassium bicarbonate solution. The mixture was stirred at 0° C. for several min and the precipitate was filtered, washed several times with water and dried in vacuo over P2O5 to obtain the titled compound (3.23 g, 94%) as a white solid.

Workup

  1. temperatureunder reflux for an additional 10 min
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringThe mixture was stirred at 0° C. for several min
  4. filtrationthe precipitate was filtered
  5. washwashed several times with water
  6. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-83e19880b15942178674c58a66ff69b7
Source dataset
uspto-grants-2004_03
Patent number
US06706717B2

Reaction notes

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