Phenyl Isothiocyanate → HCID 4485432, compound

HRID 1509758Notes

Reaction equation

HRID 1509758 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]1([N:13]=[C:14]=[S:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)(Cl)Cl>[OH:4][CH2:3][C:2]([NH:1][C:14]([NH:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[S:15])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 4485432HCID 4485432, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In 500 g of chloroform was dissolved 2-amino-2-methyl-1-propanol (61.6 g, 0.69 moL). Then, 300 g of chloroform solution containing phenyl isothiocyanate (81.6 g, 0.6 moL) was slowly added dropwise to the mixture over one hour, while stirring. Upon completion of the addition, the resulting mixture was stirred for 12 hours at room temperature. The precipitated crystals were refluxed with heat to be dissolved and then recrystallized. The crystals thus obtained were collected by filtration, washed with 20 mL of diethyl ether three times, and then dried under reduced pressure at room temperature to give 80.1 g of N-(1-hydroxy-2-methylpropan-2-yl)-N′-phenylthiourea (yield 60%).

Workup

  1. additionwas slowly added dropwise to the mixture over one hour
  2. additionUpon completion of the addition
  3. stirringthe resulting mixture was stirred for 12 hours at room temperature
  4. temperatureThe precipitated crystals were refluxed
  5. temperaturewith heat
  6. dissolutionto be dissolved
  7. customrecrystallized
  8. customThe crystals thus obtained
  9. filtrationwere collected by filtration
  10. washwashed with 20 mL of diethyl ether three times
  11. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-fce7cd6d5dc94a0f94cbe4a5e61c8f75
Source dataset
uspto-grants-2012_07
Patent number
US08211412B2

Reaction notes

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