Triethylamine → N-(2-amino-4-(4-methyl-1H-imidazol-1-yl)phenyl)-3-iodo-4-methylbenzamide

HRID 706817Notes

Reaction equation

HRID 706817 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.C(N(CC)CC)C.[NH2:19][C:20]1[CH:26]=[C:25]([N:27]2[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]2)[CH:24]=[CH:23][C:21]=1[NH2:22]>O=S(Cl)Cl.CN(C1C=CN=CC=1)C.C1COCC1>[NH2:19][C:20]1[CH:26]=[C:25]([N:27]2[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]2)[CH:24]=[CH:23][C:21]=1[NH:22][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6216403-Iodo-4-methylbenzoic acidHCID 100582902-Amino-4-(4-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 86709560N-(2-amino-4-(4-methyl-1H-imidazol-1-yl)phenyl)-3-iodo-4-methylbenzamideYield 37%

Reagents, catalysts & solvents 3

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

Procedure

A solution of 3-iodo-4-methylbenzoic acid (0.26 g, 1 mmol) in SOCl2 (5 mL) was refluxed for 2 h, and then evaporated in vacuo to remove excess SOCl2. The residue was dissolved in 5 mL anhydrous THF and added to a solution of triethylamine (0.12 g, 1.2 mmol), 2-amino-4-(4-methyl-1H-imidazol-1-yl)aniline (0.18 g, 1 mmol) and DMAP (24 mg) in 5 mL anhydrous THF in dropwise. The result mixture was stirred at rt for 20 hrs, and evaporated in vacuo. The residue was purified by chromatography on silica gel (CH2Cl2/CH3OH 97:3) to give 0.16 g product as a pale yellow solid (37.0%). LC/MS: m/z [M+H]+ 433.0520.

Workup

  1. customevaporated in vacuo
  2. customto remove excess SOCl2
  3. dissolutionThe residue was dissolved in 5 mL anhydrous THF
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel (CH2Cl2/CH3OH 97:3)

Sources & evidence

ORD record
ord-1b16d66cd5154f1986c6c2edb3a10f31
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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