Water → 2-[Bis(4-acetoxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamide

HRID 1196155Notes

Reaction equation

HRID 1196155 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[C:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([C:39]2[CH:44]=[CH:43][C:42]([O:45][C:46](=[O:48])[CH3:47])=[CH:41][CH:40]=2)[C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32](Cl)=[O:33])=[CH:25][CH:24]=1)(=[O:21])[CH3:20].O>C(Cl)Cl>[C:19]([O:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]([C:39]2[CH:40]=[CH:41][C:42]([O:45][C:46](=[O:48])[CH3:47])=[CH:43][CH:44]=2)[C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:3]=2[O:2][CH3:1])=[O:33])=[CH:27][CH:28]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 176522,4-DimethoxyanilineHCID 152967802-[Bis(4-acetoxyphenyl)methyl]benzoyl chloride

Product 1

HCID 152967812-[Bis(4-acetoxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 20 ml of methylene chloride were dissolved 1.08 g of 2,4-dimethoxyaniline and 4.5 ml of triethylamine. To this solution was dropwise added under ice cooling 20 ml of methylene chloride containing 3 g of 2-[bis(4-acetoxyphenyl)methyl]benzoyl chloride obtained in Reference Example 2. After stirring for 7 hours, water was added thereto. The organic layer was separated off, and the aqueous layer was extracted with chloroform. The chloroform layer was combined with the organic layer, and the combined organic layer was washed with 2N aqueous hydrochloric acid solution and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure to give 2.6 g of the desired product (Compound 2) as an oily matter.

Workup

  1. customobtained in Reference Example 2
  2. customThe organic layer was separated off
  3. extractionthe aqueous layer was extracted with chloroform
  4. washthe combined organic layer was washed with 2N aqueous hydrochloric acid solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fd6eafdbbb8349829b62c2373eaf3555
Source dataset
uspto-grants-1992_05
Patent number
US05112867

Reaction notes

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