Sodium Iodide → N-[(4-Chlorophenyl)methyl]-N-(5-phenylthiophen-2-yl)benzamide

HRID 1448711Notes

Reaction equation

HRID 1448711 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1.[Na+].[I-]>CN(C)C=O>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:12]([C:10]2[S:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)[C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 23341604N-(5-Phenyl-2-thienyl)-benzamide

Product 1

HCID 23341615N-[(4-Chlorophenyl)methyl]-N-(5-phenylthiophen-2-yl)benzamideYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

The amide of Example 53 (2.8 g, 0.01 mole) in dimethylformamide (25 ml.) was added to sodium hydride (0.0105 mole) (from 40-50% NaH in oil, 0.74 g) which was stirred in dimethylformamide (25 ml.) and cooled in ice. The mixture was stirred for 0.5 hr. and treated with a solution of p-chlorobenzyl chloride (3.22 g, 0.02 mole) in DMF (15 ml.) and a trace of NaI. The mixture was stirred, initially at ice-bath temperature and then at room temperature overnight and then refluxed for 3 hours to complete the reaction. The DMF was evaporated off, water was added, the product extracted with chloroform, which was dried (Na2SO4), filtered and evaporated to give the N-p-chlorobenzyl-benzamide (2.07 g.) as a viscous oil, b.p. 240°-245° C./0.35 mm. Hg.

Workup

  1. temperaturecooled in ice
  2. stirringThe mixture was stirred, initially at ice-bath temperature
  3. customthe reaction
  4. customThe DMF was evaporated off
  5. additionwater was added
  6. extractionthe product extracted with chloroform, which
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-e379b740db89492aad9d8a973416ec14
Source dataset
uspto-grants-1980_02
Patent number
US04187232

Reaction notes

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