Acetic Anhydride → HCID 178471861, compound

HRID 1584815Notes

Reaction equation

HRID 1584815 reaction equation
[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([F:17])[C:3]=1[CH3:18].[C:19](OC(=O)C)(=O)[CH3:20].CO[CH:28](OC)[N:29]([CH3:31])C.C1(N)CC1>C(Cl)Cl.C(O)C.CCCCCC>[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:5]([C:6]([C:8](=[CH:31][NH:29][CH:28]2[CH2:20][CH2:19]2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([F:17])[C:3]=1[CH3:18]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 69828CyclopropylamineHCID 78373Dimethylformamide dimethyl acetalHCID 21220244Ethyl 4-bromo-2,5-difluoro-3-methylbenzoylacetate

Product 1

HCID 178471861HCID 178471861, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

In 150 ml of methylene chloride was dissolved 30.0 g of ethyl 4-bromo-2,5-difluoro-3-methylbenzoylacetate, and 19.1 g of acetic anhydride and 22.3 g of N,N-dimethylformamide dimethyl acetal were added to the solution, after which the resulting mixture was stirred at room temperature for one hour. Thereafter, the solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in 90 ml of ethanol and 5.90 g of cyclopropylamine was added thereto, after which the resulting mixture was stirred at room temperature for 30 minutes. The solvent was then removed by distillation under reduced pressure. To the residue obtained was added n-hexane and the crystals formed were collected by filtration, to obtain 35.7 g of colorless, crystalline ethyl 2-(4-bromo-2,5-difluoro-3-methylbenzoyl)-3-cyclopropylaminoacrylate.

Workup

  1. additionwere added to the solution
  2. customThereafter, the solvent was removed by distillation under reduced pressure
  3. customThe residue obtained
  4. stirringafter which the resulting mixture was stirred at room temperature for 30 minutes
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customTo the residue obtained
  7. customthe crystals formed
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-da6ad9c6b29049c28b13c1b9c483af8a
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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