1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride → 3-Chloro-4-(trifluoromethyl)phenoxyl-N-{3-methyl-4-[(methylsulfonyl)amino]benzyl}acetamide

HRID 1350827Notes

Reaction equation

HRID 1350827 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[O:5][CH2:6][C:7]([OH:9])=O.[Cl-].ClC1N(C)CC[NH+]1C.Cl.[NH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[C:31]([CH3:40])[CH:30]=1>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[O:5][CH2:6][C:7]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[C:31]([CH3:40])[CH:30]=1)=[O:9]

Participants

5

Reactant 3

HCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 21097484[3-Chloro-4-(trifluoromethyl)phenoxy]acetic acidHCID 21097529N-[4-(aminomethyl)-2-methylphenyl]methanesulfonamide hydrochloride

Product 1

HCID 116695923-Chloro-4-(trifluoromethyl)phenoxyl-N-{3-methyl-4-[(methylsulfonyl)amino]benzyl}acetamideYield 67%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

[3-Chloro-4-(trifluoromethyl)phenoxy]acetic acid (127 mg, 0.5 mmol), 2-chloro-1,3-dimethylimidazolinium chloride (CDI) (97 mg, 0.6 mmol), triethylamine (0.33 ml) and N{4-(aminomethyl)-2-methylphenyl]methanesulfonamide hydrochloride (151 mg, 0.6 mmol) were treated in the same procedure described in Example 2(b). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethyl acetate (3/1 to 1/1) to furnish 150 mg (67% yield) of the title compound as a white solid.

Workup

  1. washeluted with a volume mixture of hexane and ethyl acetate (3/1 to 1/1)

Sources & evidence

ORD record
ord-37b36ae4724240e8a28d897160a28d48
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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