Diethyl Ether → HCID 12427468, compound

HRID 1605687Notes

Reaction equation

HRID 1605687 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[NH2:16])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CCOCC.[Cl:29][C:30]([Cl:35])([Cl:34])[C:31](Cl)=[O:32]>C(Cl)Cl>[CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[NH:16][C:31](=[O:32])[C:30]([Cl:35])([Cl:34])[Cl:29])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 745192-Amino-5-chlorophenyl cyclohexyl ketone

Product 1

HCID 12427468HCID 12427468, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 14.3 g of 2-amino-5-chlorophenyl cyclohexyl ketone and 6.0 g of triethylamine in the mixture of 100 ml of ether and 30 ml of methylene chloride was added dropwise with ice-cooling 11.0 g of trichloroacetyl chloride. After the mixture was stirred at room temperature for 2 hours, the organic layer was washed with water and dried over anhydrous sodium sulfate. Then the solvent was removed under reduced pressure to give oily residue. The residue was crystallized from ether to obtain 18.5 g of 2-trichloroacetamido-5-chlorophenyl cyclohexyl ketone as light yellow crystals, m.p. 93.0°-93.5°C.

Workup

  1. additionwas added dropwise with ice-
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThen the solvent was removed under reduced pressure
  5. customto give oily residue
  6. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-2f6acc7e1ba0447b8374695988b0910c
Source dataset
uspto-grants-1976_04
Patent number
US03950526

Reaction notes

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