Triethylamine → HCID 86749462, compound

HRID 362341Notes

Reaction equation

HRID 362341 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[I:17].C(N(CC)CC)C.[N+:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)([O-:27])=[O:26]>O1CCCC1>[N+:25]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([C:7]2[C:2]([I:1])=[C:3]([CH2:8][CH2:9][NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[I:17])[CH:4]=[CH:5][CH:6]=2)=[O:33])=[CH:35][CH:36]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 53939659HCID 53939659, compound

Product 1

HCID 86749462HCID 86749462, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.90 g of 2-iodo-N-(2-iodophenyl)benzeneethanamine in 4 ml of tetrahydrofuran is added 0.41 g of triethylamine, and 0.57 g of 4-nitrobenzoyl chloride. The mixture is stirred at room temperature for 2 hours and the solvent removed under vacuum. The residue is dissolved in ethyl acetate-dichloromethane (5:1) and the solution washed with 1N HCl, saturated NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate. The filtrate is evaporated and the residual solid triturated with diethyl ether and hexane to give 1.10 g of product as a white solid.

Workup

  1. customthe solvent removed under vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate-dichloromethane (5:1)
  3. washthe solution washed with 1N HCl, saturated NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  6. customThe filtrate is evaporated
  7. customthe residual solid triturated with diethyl ether and hexane

Sources & evidence

ORD record
ord-c78cb77f92604b42bf9ed2a78aa30f41
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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