3-(Trifluoromethyl)benzoic acid → N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 2041906Notes

Reaction equation

HRID 2041906 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](O)=[O:16].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C1COCC1.O>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[C:12]([C:11]([F:10])([F:21])[F:22])[CH:13]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

7

Reactant 4

HCID 99633-(Trifluoromethyl)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 1188893-Iodo-p-toluidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 7925506N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-iodo-4-methylaniline (1.22 g, 5.25 mmol), 3-(trifluoromethyl)benzoic acid (0.95 g, 5 mmol), HOBt (0.68 g, 5 mmol), and EDCl (1.05 g, 5.5 mmol) in THF (20 mL) was stirred overnight at rt. Water was added and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, concentrated on a rotavap, and then subjected to silica gel column chromatography (3:1 hexane/ethyl acetate) yielding the desired product.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated on a rotavap

Sources & evidence

ORD record
ord-068994dabe4b405a8447bfddafd3073f
Source dataset
uspto-grants-2013_11
Patent number
US08586566B2

Reaction notes

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