Ethyl Acetate → HCID 136404501, compound

HRID 2165733Notes

Reaction equation

HRID 2165733 reaction equation
[Br: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.[CH3:20][N:21]([CH3:26])[C:22](=[S:25])[NH:23][NH2:24].C(OCC)(=O)C>C(O)C>[BrH:1].[C:16]([C:7]1[CH:6]=[C:5]([C:3]2[CH2:2][S:25][C:22]([N:21]([CH3:26])[CH3:20])=[N:23][N:24]=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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-oneHCID 27337004,4-Dimethyl-3-thiosemicarbazide

Product 1

HCID 136404501HCID 136404501, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

196.4 g (0.6 mol) of 2-bromo-1-(3,5-di-tert.butyl-4-hydroxyphenyl)-ethanone from step (a) and 59.6 g (0.5 mol) of 4,4-dimethylthiosemicarbazide were suspended in 1500 ml of ethanol and slowly heated to 70° C. while stirring, a clear solution being produced. The solution was stirred at this temperature for 10 minutes and then cooled, and the solvent was removed under reduced pressure. Washing the residue, produced as an oil, by stirring with 500 ml of ethyl acetate produced a batch of crystals, which was again briefly heated to boiling in 500 ml of ethyl ester. The crystalline product was filtered off, washed with 150 ml of ethyl acetate and dried in a vacuum cabinet.

Workup

  1. customa clear solution being produced
  2. stirringThe solution was stirred at this temperature for 10 minutes
  3. temperaturecooled
  4. customthe solvent was removed under reduced pressure
  5. washWashing the residue
  6. customproduced as an oil
  7. customproduced a batch of crystals, which
  8. temperaturewas again briefly heated
  9. filtrationThe crystalline product was filtered off
  10. washwashed with 150 ml of ethyl acetate
  11. customdried in a vacuum cabinet

Sources & evidence

ORD record
ord-fdbea1e45756401d90af2968345d7f2a
Source dataset
uspto-grants-1990_07
Patent number
US04940790

Reaction notes

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