1,2-Dichloroethane → 4-Iodo-N-[2-(phenylamino)phenyl]benzamide

HRID 420455Notes

Reaction equation

HRID 420455 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.ClCCCl.S(Cl)(Cl)=O.[C:19]1([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH2:32])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[NH:25][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 120854-Iodobenzoic acidHCID 24386Thionyl ChlorideHCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 230940774-Iodo-N-[2-(phenylamino)phenyl]benzamideYield 96.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 962WaterSolvent

Procedure

Suspending 5.0 g (20 mmol) of 4-iodobenzoic acid into 50 milliliter of 1,2-dichloroethane, added 3 drops of N,N-dimethylformamide. Further adding 3.6 g (30 mmol) of thionyl chloride, the resultant suspension was refluxed with heating for 2 hours. Subsequently, removing the solvent by distillation, the residue was dissolved into 50 milliliter of N-methylpyrrolidone and then, further adding 3.7 g (20 mmol) of N-phenyl-1,2-phenylenediamine, the resultant solution was stirred at room temperature for 5 hours. After completion of the reaction, adding water and filtering the precipitated solid, washing with water and further with methanole, 8.0 g of crude 4-iodo-N-(2-phenylamino-phenyl)-benzamide was obtained.

Workup

  1. temperaturewith heating for 2 hours
  2. customSubsequently, removing the solvent
  3. distillationby distillation
  4. dissolutionthe residue was dissolved into 50 milliliter of N-methylpyrrolidone
  5. customAfter completion of the reaction
  6. filtrationfiltering the precipitated solid
  7. washwashing with water and further with methanole

Sources & evidence

ORD record
ord-6f16048c5ea94043b77799a12116a366
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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