Sodium Hydroxide → (5-Bromo-2,4-difluoro-phenyl)-thiourea

HRID 2068685Notes

Reaction equation

HRID 2068685 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([Br:19])[C:16]([F:20])=[CH:15][C:14]=1[F:21])=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1.O>[Br:19][C:17]1[C:16]([F:20])=[CH:15][C:14]([F:21])=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 596030931-Benzoyl-3-(5-bromo-2,4-difluoro-phenyl)-thiourea

Product 1

HCID 59603071(5-Bromo-2,4-difluoro-phenyl)-thioureaYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 1-benzoyl-3-(5-bromo-2,4-difluoro-phenyl)-thiourea II (1.70 g, 4.60 mmol) in THF (35.0 mL) was added a solution of NaOH (0.97 g, 24.25 mmol) in water (13.0 mL). The resulting reaction mixture was stirred at 70° C. for 15 h. After the completion of the reaction (TLC monitoring), THF was evaporated, added water and extracted with EtOAc (3×50 mL). The combined organics was washed with brine and concentrated to obtain the desired compound (1.0 g, 83%). MS: 267.03 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customwas evaporated
  3. additionadded water
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined organics was washed with brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb25d031c2e64ceaa5df3d96e5da9d85
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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