Sodium Hydroxide → HCID 58033225, compound

HRID 447065Notes

Reaction equation

HRID 447065 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([Br:19])[N:16]=[C:15]([Br:20])[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1>[Br:20][C:15]1[CH:14]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:18]=[C:17]([Br:19])[N:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58033240HCID 58033240, compound

Product 1

HCID 58033225HCID 58033225, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
62.5 °C

Procedure

To a solution of 1-benzoyl-3-(2,6-dibromo-pyridin-4-yl)-thiourea (1.0 g, 2.14 mmol) in THF (50 mL) was added NaOH solution (0.48 in 20 mL H2O) at room temperature. The reaction mixture was heated up to 60-65° C. overnight. After completion of reaction (TLC monitoring) THF was distilled off followed by addition of water, and extraction with ethyl acetate (2×50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude residue was washed with mixture of ethyl acetate:hexane (30:70) and dried under high vacuum to get the desired product as a white solid (0.58 g, 78%).

Workup

  1. distillationwas distilled off
  2. additionfollowed by addition of water, and extraction with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. washThe crude residue was washed with mixture of ethyl acetate:hexane (30:70)
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-147f7f3873a04c048314a561558492fe
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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