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

HRID 27667
Notes
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Reaction equation

HRID 27667 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent
3×

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 them 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 and them at room temperature overnight
  3. temperaturerefluxed for 3 hours
  4. customthe reaction
  5. customThe DMF was evaporated off
  6. additionwater was added
  7. extractionthe product extracted with chloroform, which
  8. dry with materialwas dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-addf2b9ec90943a3879b3d89bdf657d3
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04222946

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes