Sodium Hydroxide → HCID 20157487, compound

HRID 1010633Notes

Reaction equation

HRID 1010633 reaction equation
[OH-].[Na+].C([NH:11][C:12]([NH:14][C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[C:17]([Br:22])[CH:16]=1)=[S:13])(=O)C1C=CC=CC=1>O.C1COCC1>[Br:21][C:19]1[CH:20]=[C:15]([NH:14][C:12]([NH2:11])=[S:13])[CH:16]=[C:17]([Br:22])[CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57813580HCID 57813580, compound

Product 1

HCID 20157487HCID 20157487, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of NaOH (46.30 g, 1.16 mol) dissolved in 480 mL of H2O was added to a solution of 1-benzoyl-3-(3,5-dibromo-phenyl)-thiourea (96.0 g, 0.23 mol) in 1.20 L of THF. The resulting reaction mixture was stirred at 70° C. for 12 hours. THF was distilled off and extracted with ethyl acetate (×3). The combined organic layer was dried over Na2SO4, filtered and distilled off to get the crude residue that was washed with hexane to obtain the desired compound as a grey solid (68 g, 95%).

Workup

  1. customThe resulting reaction mixture
  2. distillationTHF was distilled off
  3. extractionextracted with ethyl acetate (×3)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. distillationdistilled off
  7. customto get the crude residue that
  8. washwas washed with hexane

Sources & evidence

ORD record
ord-c727c6556b6246e2a939c0c145d69d71
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

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