Triethylamine → 3-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide

HRID 80600Notes

Reaction equation

HRID 80600 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[CH3:12][C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:19]=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:21]=[C:22]([NH2:24])[CH:23]=2)[CH:17]=1.CCN(CC)CC>CN(C=O)C.O=S(Cl)Cl.C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:24][C:22]1[CH:21]=[C:20]([C:25]([F:26])([F:27])[F:28])[CH:19]=[C:18]([N:16]2[CH:17]=[C:13]([CH3:12])[N:14]=[CH:15]2)[CH:23]=1)=[O:7]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6216403-Iodo-4-methylbenzoic acidHCID 120028253-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline2×

Product 1

HCID 177521583-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Add 2 drops of DMF into 628 mg 3-iodo-4-methylbenzoic acid (2.2 mmol) in 20 mL SOCl2 and reflux for 2 h. After vacuum evaporation of SOCl2, add 6.0 mL anhydrous THF and get the pale yellow solution. Dissolve the product from step 1, 524 mg 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine (2.0 mmol) in 6.0 mL anhydrous THF and add 10 mmol Et3N, and the pale yellow solution prepared previously is added drop wise till it is all added. The reaction mixture rises to room temperature for 1 hr. The reaction was quenched with addition of brine and extracted with EtOAc. The combined extraction organic layers was dried and concentrated under vacuum, the residue was purified through column chromatography to afford 873 mg desired product. (90%)

Workup

  1. temperaturereflux for 2 h
  2. customAfter vacuum evaporation of SOCl2
  3. additionadd 6.0 mL anhydrous THF
  4. customget the pale yellow solution
  5. customthe pale yellow solution prepared previously
  6. additionis added drop wise till it
  7. customThe reaction was quenched with addition of brine
  8. extractionextracted with EtOAc
  9. extractionThe combined extraction organic layers
  10. customwas dried
  11. concentrationconcentrated under vacuum
  12. customthe residue was purified through column chromatography

Sources & evidence

ORD record
ord-9353afddde6a40db92edc3cb59c3eac4
Source dataset
uspto-grants-2014_09
Patent number
US08846671B2

Reaction notes

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