Water → HCID 19025404, compound

HRID 1030988Notes

Reaction equation

HRID 1030988 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=1[F:14])[CH3:2].O.[C:16](OC(=O)C)(=[O:18])[CH3:17]>S(=O)(=O)(O)O>[CH2:1]([N:3]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=1[F:14])[C:16](=[O:18])[CH3:17])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 19025399HCID 19025399, compound

Product 1

HCID 19025404HCID 19025404, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a stirred mixture of 5.4 g (0.027 mole) of N-ethyl-2,5-difluoro-4-nitroaniline in 100 ml of acetic anhydride was added three drops of concentrated sulfuric acid. This mixture was stirred at room temperature for 30 minutes, and was poured into 200 ml of ice and water. The aqueous mixture was extracted with three portions of ethyl acetate. The extracts were combined and washed in succession with an aqueous, saturated sodium chloride solution and water. The washed organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure to yield 6.1 g of N-ethyl-N-(2,5-difluoro-4-nitrophenyl)acetamide as a solid. The nmr spectrum was consistent with the proposed structure.

Workup

  1. extractionThe aqueous mixture was extracted with three portions of ethyl acetate
  2. washwashed in succession with an aqueous, saturated sodium chloride solution and water
  3. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-444f2ed80ca54cd5b183a57f1887ed7e
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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