Iodoethane → HCID 10934202, compound

HRID 839501Notes

Reaction equation

HRID 839501 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].[H-].[Na+].[CH2:19](I)[CH3:20]>O>[CH2:19]([NH:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:20]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 128702-Amino-5-chlorobenzophenoneHCID 24758Sodium hydride

Product 1

HCID 10934202HCID 10934202, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6.95 g of 2-amino-5-chlorobenzophenone was added portionwise 1.37 g of 63 % sodium hydride. After the mixture was stirred at room temperature for 30 minutes, 5.62 g of ethyl iodide was added dropwise thereto, and the reaction mixture was further stirred at room temperature for 2 hours. Then, the mixture was poured into 400 ml of water and extracted twice with 100 ml of methylene chloride. The extracts were combined, washed with diluted hydrochloric acid, followed by water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel using chloroform as an eluent to give 7.1 g of 2-ethylamino-5-chlorobenzophenone as red oil, which was recrystalized from ethanol-cyclohexane to give yellow prisms having a melting point of 57° - 58° C.

Workup

  1. stirringthe reaction mixture was further stirred at room temperature for 2 hours
  2. extractionextracted twice with 100 ml of methylene chloride
  3. washwashed with diluted hydrochloric acid
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-62ed7aec7f044bcb9087ef909cb91e07
Source dataset
uspto-grants-1978_06
Patent number
US04096144

Reaction notes

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