Acetic Anhydride → HCID 1482611, compound

HRID 1257301Notes

Reaction equation

HRID 1257301 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:13]([O-])([O-])OCC.C(OC(=O)C)(=O)C.[NH2:26][NH:27][C:28]([NH2:30])=[S:29].Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=1)=O>C(O)C>[Cl:42][C:37]1[CH:36]=[C:35]([C:33]2[N:30]=[C:28]([N:27]3[C:3]([C:2]([F:12])([F:11])[F:1])=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:13]=[N:26]3)[S:29][CH:32]=2)[CH:40]=[CH:39][C:38]=1[Cl:41]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 2723789ThiosemicarbazideHCID 53630039Ethylorthoformate

Product 1

HCID 1482611HCID 1482611, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4,4,4-trifluoroacetoacetate (3.59 g, 19.5 mmol), ethyl orthoformate (4.49 mL, 27 mmol) and acetic anhydride (5.10 mL, 54 mmol) was heated under reflux for 3.5 hr, and the mixture was concentrated under reduced pressure. Ethanol (50 mL) and thiosemicarbazide (1.37 g, 15 mmol) were added, and the reaction mixture was stirred at room temperature for 2.5 hr. 2-Bromo-1-(3,4-dichlorophenyl)ethanone (4.02 g, 15 mmol) was added, and the mixture was stirred at 80° C. for 30 min, cooled to room temperature. The precipitated crystals were collected by filtration to give a crude title compound (4.73 g, 72%) as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 hr
  3. concentrationthe mixture was concentrated under reduced pressure
  4. stirringthe mixture was stirred at 80° C. for 30 min
  5. temperaturecooled to room temperature
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-565179ce8afb462ca86169ea740fab89
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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