Sodium Hydroxide → (3-Benzyloxy-5-bromo-phenyl)thiourea

HRID 1941976Notes

Reaction equation

HRID 1941976 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[C:15]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1.O>[CH2:21]([O:20][C:15]1[CH:14]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:18]=[C:17]([Br:19])[CH:16]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57813640N-[(3-benzyloxy-5-bromophenyl)carbamothioyl]benzamide

Product 1

HCID 57813605(3-Benzyloxy-5-bromo-phenyl)thioureaYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To an ice-cold solution of 1-benzoyl-3-(3-benzyloxy-5-bromo-phenyl)thiourea (33.0 g, 74.70 mmol) in THF (500.0 mL) was added a solution of NaOH (15.0 g, 375.0 mmol) in H2O (180.0 mL). The resulting reaction mixture was stirred at 65° C. for 15 h. The reaction mass was then cooled to room temperature, added water and extracted with EtOAc (3×1.0 L). The combined organics was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure to get the desired compound (23.50 g, 94%) that was carried forward to the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mass was then cooled to room temperature
  3. extractionextracted with EtOAc (3×1.0 L)
  4. washThe combined organics was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de3ce3d84a684e818b7720477b2bd01a
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

Loading…