Ethyl Acetate → HCID 178513381, compound

HRID 2046566Notes

Reaction equation

HRID 2046566 reaction equation
Cl[N:2]1C(=O)CCC1=O.[Br:9][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([F:20])[C:11]=1[CH:12]=[N:13][OH:14].[NH4+].[OH-].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[Br:9][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([F:20])[C:11]=1[C:12]([NH:13][OH:14])=[NH:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 31398ChlorosuccinimideHCID 866672572-Bromo-4-chloro-6-fluorobenzaldehyde oxime

Product 1

HCID 178513381HCID 178513381, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N-chlorosuccinimide (8.34 g, 62.49 mmol) in DMF (25 ml) was added slowly to a solution of 2-bromo-4-chloro-6-fluoro-benzaldehyde oxime (15 g, 59.52 mmol) in DMF (50 ml) at 50° C. After completion of the addition, the reaction mixture was allowed to stir for 30 minutes at 50° C. It was then cooled to 3-5° C. and NH4OH (4.6 ml, 119 mmol) was added dropwise. During addition the temperature was maintained between 0-10° C. and the reaction mixture was stirred for another 15 minutes at the same temperature. EtOAc and brine were then added and the mixture was agitated vigorously for 10 minutes before the phases were allowed to settle. The aqueous layer was separated and extracted two times with EtOAc. The combined organic layers were dried with Na2SO4 and evaporated to obtain the title compound (13 g, 82%) as off white solid.

Workup

  1. additionAfter completion of the addition
  2. temperatureIt was then cooled to 3-5° C.
  3. additionDuring addition the temperature
  4. temperaturewas maintained between 0-10° C.
  5. stirringthe reaction mixture was stirred for another 15 minutes at the same temperature
  6. stirringthe mixture was agitated vigorously for 10 minutes before the phases
  7. customThe aqueous layer was separated
  8. extractionextracted two times with EtOAc
  9. dry with materialThe combined organic layers were dried with Na2SO4
  10. customevaporated

Sources & evidence

ORD record
ord-db32c9b8e5ba46b4872682aeb9204e44
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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