Sodium Hydroxide → HCID 5079711, compound

HRID 1509759Notes

Reaction equation

HRID 1509759 reaction equation
O[CH2:2][C:3]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[S:8])([CH3:5])[CH3:4].[OH-].[Na+]>Cl>[CH3:2][C:3]1([CH3:5])[CH2:4][S:8][C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4485432HCID 4485432, compound

Product 1

HCID 5079711HCID 5079711, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

N-(1-hydroxy-2-methylpropan-2-yl)-N′-phenylthiourea (80.1 g, 0.36 mol) was dissolved in 2,400 mL of 35% HCl, and the resulting mixture was stirred while heating at 90° C. for 1.5 hours. After cooling, the mixture was neutralized with NaOH and extracted with diethyl ether. The extract was washed with saturated brine and then anhydrous sodium sulfate was added. The organic phase was distilled off under reduced pressure and the residue was washed three times with hexane. The crystals thus obtained were dried under reduced pressure at room temperature, and then recrystallized from methanol twice to give 22.4 g of the title compound (yield 18%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with saturated brine
  4. additionanhydrous sodium sulfate was added
  5. distillationThe organic phase was distilled off under reduced pressure
  6. washthe residue was washed three times with hexane
  7. customThe crystals thus obtained
  8. customwere dried under reduced pressure at room temperature
  9. customrecrystallized from methanol twice

Sources & evidence

ORD record
ord-7a32aad737b84f48a2049b60a306901b
Source dataset
uspto-grants-2012_07
Patent number
US08211412B2

Reaction notes

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