Water → STK173631

HRID 743054Notes

Reaction equation

HRID 743054 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C(N(CC)CC)C.[Cl:24][C:25]([Cl:30])([Cl:29])[C:26](Cl)=[O:27].O>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:2]([NH:1][C:26](=[O:27])[C:25]([Cl:30])([Cl:29])[Cl:24])=[C:3]([CH:12]=1)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 128702-Amino-5-chlorobenzophenone

Product 1

HCID 306974STK173631Yield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 23.2 g (100 mmol) of 2-amino-5-chlorobenzophenone and 11 g (110 mmol) of triethylamine in 200 mL of tetrahydrofuran was added dropwise 20 g (110 mmol) of trichloroacetyl chloride at temperature of 5° C. to 15° C. After being stirred for 3 hours at ambient temperature, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer separated was washed with water and then with brine, dried on anhydrous sodium sulfate and concentrated in vacuo. The resulting crude crystals were recrystallized from ethanol to give 33.8 g (89.9 mmol) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer separated
  3. washwas washed with water
  4. dry with materialwith brine, dried on anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-11d5499ad90c4e189ca6f752fc1c6077
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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