HCID 12213679, compound → HCID 178482493, compound

HRID 2165737Notes

Reaction equation

HRID 2165737 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)=O.Cl.[CH3:21][NH:22][C:23](=[S:26])[NH:24][NH2:25]>C(O)C>[ClH:1].[C:16]([C:7]1[CH:6]=[C:5]([C:3]2[CH2:2][S:26][C:23]([NH:22][CH3:21])=[N:24][N:25]=2)[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]=1[OH:15])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 12213679HCID 12213679, compoundHCID 142109772-Chloro-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 178482493HCID 178482493, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.7 g (0.038 mol) of 2-chloro-1-(3,5-di-tert.butyl-4-hydroxyphenyl)-ethanone from step (a) and 4.8 g (0.034 mol) of 4-methylthiosemicarbazide hydrochloride were dissolved in 120 ml of ethanol, and the mixture was heated to boiling for 30 minutes. After cooling, the solvent was removed by distillation under reduced pressure, and the resinous residue was dissolved in 60 ml of warm ethyl acetate. On standing, the product immediately precipitated in crystalline form, and was filtered off and recrystallized again from 150 ml of a mixture of ethyl acetate and methylene chloride (10 : 1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. customthe solvent was removed by distillation under reduced pressure
  4. dissolutionthe resinous residue was dissolved in 60 ml of warm ethyl acetate
  5. customthe product immediately precipitated in crystalline form
  6. filtrationwas filtered off
  7. customrecrystallized again from 150 ml of a mixture of ethyl acetate and methylene chloride (10 : 1)

Sources & evidence

ORD record
ord-c2a05258086f44e29a52a9932875e788
Source dataset
uspto-grants-1990_07
Patent number
US04940790

Reaction notes

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