Water → 2-Trichloroacetylamino-3'-methoxybenzophenone

HRID 479464Notes

Reaction equation

HRID 479464 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[O:5].C(N(CC)CC)C.[Cl:25][C:26]([Cl:31])([Cl:30])[C:27](Cl)=[O:28].O>O1CCCC1>[Cl:25][C:26]([Cl:31])([Cl:30])[C:27]([NH:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[O:5])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 22135242(2-Aminophenyl)(3-methoxyphenyl)methanone

Product 1

HCID 187709012-Trichloroacetylamino-3'-methoxybenzophenoneYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.89 g (12.7 mmol) of 2-amino-3′-methoxybenzophenone and 2.13 ml (15.2 mmol) of triethylamine in 16 ml of tetrahydrofuran (THF), 1.56 ml (14 mmol) of trichloroacetyl chloride were added dropwise under ice-cooling and stirred for 2 hours. Water was added to the reaction mixture, which was followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give 4.51 g (12.1 mmol) of the title compound.

Workup

  1. temperaturecooling
  2. extractionwas followed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-6b6bcda673f4461282dc777b2a2b0848
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

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