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

HRID 712149Notes

Reaction equation

HRID 712149 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]([NH:19]C(=O)C2C=CC=CC=2)=[S:18])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]([NH2:19])=[S:18])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 57813605(3-Benzyloxy-5-bromo-phenyl)thioureaYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
69.5 °C

Procedure

To a solution of N-[(3-benzyloxy-5-bromo-phenyl)carbamothioyl]benzamide (648 g, 1.47 mol) in THF (12 L) was added NaOH solution (300 g, 7.5 mol in 3 L H2O) at rt. The reaction mixture was heated up to 69 to 70° C. overnight. After completion of reaction (by TLC), the THF layer was decanted off and the aqueous layer extracted with EtOAc (3×2 L). The combined organic layer (THF+EtOAc) was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was treated with mixture of Et2O and hexane (5:95, 3.0 L), filtered, washed with hexane and dried under high vacuum to obtain the desired product (387 g, 78%).

Workup

  1. customAfter completion of reaction (by TLC)
  2. customthe THF layer was decanted off
  3. extractionthe aqueous layer extracted with EtOAc (3×2 L)
  4. washThe combined organic layer (THF+EtOAc) was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionThe crude residue was treated with mixture of Et2O and hexane (5:95, 3.0 L)
  9. filtrationfiltered
  10. washwashed with hexane
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-96a5415264e84bc399f4823d511a7fb3
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…