Diethyl Ether → 2-[4-(1-Hydroxy-1-methylethyl)benzoylamino]-N-(4-methoxyphenyl)benzamide

HRID 395713Notes

Reaction equation

HRID 395713 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][C:11]2[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:14])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:30][Mg]Br.C(OCC)C>O1CCCC1>[OH:3][C:1]([C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][C:11]2[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:14])=[O:9])=[CH:6][CH:5]=1)([CH3:30])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 106439802-(4-Acetylbenzoylamino)-N-(4-methoxyphenyl)benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 117955102-[4-(1-Hydroxy-1-methylethyl)benzoylamino]-N-(4-methoxyphenyl)benzamideYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-acetylbenzoylamino)-N-(4-methoxyphenyl)benzamide (161 mg, 0.410 mmol) in tetrahydrofuran (10 mL) cooled to 0° C. was added 3 M methyl magnesium bromide in diethyl ether (0.2 mL, 0.6 mmol). After 1 h, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (2 mL), diluted with ether, and washed with water. The organic layer. was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was chromatographed (silica gel, 15% ethyl acetate/85% hexanes to 35% ethyl acetate/65% hexanes) to give 24 mg (14%) of the title compound as a white solid.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride solution (2 mL)
  2. additiondiluted with ether
  3. washwashed with water
  4. dry with materialwas dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (silica gel, 15% ethyl acetate/85% hexanes to 35% ethyl acetate/65% hexanes)

Sources & evidence

ORD record
ord-47163348016c448c9dd91ece419a82a9
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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