Water → HCID 23504053, compound

HRID 1835615Notes

Reaction equation

HRID 1835615 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[Br:9]Br.[C:11]([NH:14][C:15]([NH2:17])=[S:16])(=[O:13])[CH3:12].O>CO>[BrH:9].[C:11]([NH:14][C:15]1[S:16][C:5]2[CH2:6][C:1](=[O:8])[CH2:2][CH2:3][C:4]=2[N:17]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 125111,4-CyclohexanedioneHCID 24408BromineHCID 2723593Acetylthiourea

Product 1

HCID 23504053HCID 23504053, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

8.8 g of 1,4-cyclohexanedione was dissolved in 40 ml of methanol. The solution was cooled on an ice bath to 10° C. and 4.4 ml of bromine was added dropwise in 10 minutes. The solution was stirred at the same temperature for 1.5 hours and then the temperature was allowed to rise to ambient. After the colour disappeared, 11.1 g of N-acetylthiourea and 20 ml of water were added and the solution was heated under reflux for 2 hours. Hot reaction mixture was filtered, the filtration cake was washed with hot methanol and the combined filtrates were heated to reflux with activated charcoal. The hot suspension was filtered and the filtrate was concentrated in vacuo to yield 3.4 g of a solid product.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationHot reaction mixture was filtered
  4. washthe filtration cake was washed with hot methanol
  5. temperaturethe combined filtrates were heated
  6. temperatureto reflux with activated charcoal
  7. filtrationThe hot suspension was filtered
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a3490ca8acf5401a9d06e06870e72f3c
Source dataset
uspto-grants-2004_08
Patent number
US06770761B2

Reaction notes

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