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

HRID 1527866Notes

Reaction equation

HRID 1527866 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]([NH2:28])[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=2)[CH:17]=1.C(N(CC)C(C)C)(C)C>O=S(Cl)Cl.CN(C1C=CN=CC=1)C.C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:28][C:20]1[CH:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=[C:18]([N:16]2[CH:17]=[C:13]([CH3:12])[N:14]=[CH:15]2)[CH:19]=1)=[O:7]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 6216403-Iodo-4-methylbenzoic acidHCID 120028253-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

3-Iodo-4-methylbenzoic acid (2.62 g, 10 mmol) was refluxed in SOCl2 (10 mL) for 1 h. The volatile components were removed on a rotavap and the residue was dissolved in benzene (10 mL), concentrated to dryness on a rotavap and further dried under vacuum. The resulting acyl chloride was added to a solution 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzenamine (2.48 g, 10.2 mmol), N,N-diisopropylethylamine (1.56 g, 12 mmol), and a catalytic amount of DMAP in THF (20 mL). After stirring at rt for 2 h, the reaction was quenched with water. EtOAc was added and the layers separated. The combined organic layers were concentrated to dryness and used without purification in next step.

Workup

  1. customThe volatile components were removed on a rotavap
  2. dissolutionthe residue was dissolved in benzene (10 mL)
  3. concentrationconcentrated to dryness on a rotavap
  4. customfurther dried under vacuum
  5. customthe reaction was quenched with water
  6. additionEtOAc was added
  7. customthe layers separated
  8. concentrationThe combined organic layers were concentrated to dryness
  9. customused without purification in next step

Sources & evidence

ORD record
ord-eaa971a6073d47399a0ba8a83a3d921a
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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