Benzyl Bromide → Methyl 2-(benzyloxy)-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate

HRID 853439Notes

Reaction equation

HRID 853439 reaction equation
[CH3:1][C:2]1([CH3:23])[O:7][C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([OH:21])[CH:12]=2)[C:4](=[O:22])[O:3]1.[H-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O.O>[CH2:26]([O:21][C:13]1[CH:12]=[C:11]([NH:10][CH:9]=[C:5]2[C:4](=[O:22])[O:3][C:2]([CH3:23])([CH3:1])[O:7][C:6]2=[O:8])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22936485Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-hydroxybenzoate

Product 1

HCID 22936598Methyl 2-(benzyloxy)-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoateYield 86.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

After suspending methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-hydroxybenzoate (13.975 g, 43.5 mmol) in dimethylformamide (140 ml) at room temperature under a nitrogen atmosphere, sodium hydride (1.87 g, 46.8 mmol) was gradually added. After 1.5 hours, benzyl bromide 5.7 ml, 47.9 mmol) was added dropwise and the mixture was stirred for 2 days. The reaction solution was diluted with water (700 ml) and stirred overnight, and the precipitated crystals were filtered, washed with diethyl ether and dried at 70° C. to obtain the title compound (15.477 g, 37.6 mmol, 86.5%) as white crystals.

Workup

  1. customat room temperature
  2. stirringstirred overnight
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with diethyl ether
  5. customdried at 70° C.

Sources & evidence

ORD record
ord-39be2a607df74f449e7e35c267a6d884
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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