2-Methoxybenzoyl chloride → N-[2-[[2,6-bis(1-Methylethyl)phenyl]amino]-2-oxoethyl]-N-(diphenylmethyl)-2-methoxybenzamide

HRID 465660Notes

Reaction equation

HRID 465660 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH3:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[C:16]=1[NH:24][C:25](=[O:41])[CH2:26][NH:27][CH:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:14]>C(N(CC)CC)C>[CH3:14][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:22])[CH3:23])[C:16]=1[NH:24][C:25](=[O:41])[CH2:26][N:27]([CH:28]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[O:2][CH3:1])[CH3:12]

Participants

4

Reactant 2

HCID 889692-Methoxybenzoyl chlorideHCID 1645639N-[2,6-bis(1-Methylethyl)phenyl]-2-[(diphenylmethyl)amino]acetamide

Product 1

HCID 19874995N-[2-[[2,6-bis(1-Methylethyl)phenyl]amino]-2-oxoethyl]-N-(diphenylmethyl)-2-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Methoxy benzoyl chloride (0.65 g) was added to a mixture of 1.50 g the product of Example 4 and excess triethylamine in 100 mL EtoAc. The reaction mixture was allowed to sit 2 days at room temperature and was then concentrated to dryness, the residue dissolved in 250 mL CH2Cl2, the organic solution washed with dilute sulfuric acid, brine, potassium carbonate solution, and brine. The solution was dried over MgSO4, filtered, and concentrated to an oil which crystallized upon addition of 1/1, hexane/EtoAc to give the title compound. Total yield, 1.53 g (76%).

Workup

  1. concentrationwas then concentrated to dryness
  2. dissolutionthe residue dissolved in 250 mL CH2Cl2
  3. washthe organic solution washed with dilute sulfuric acid, brine, potassium carbonate solution, and brine
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil which
  7. customcrystallized upon addition of 1/1, hexane/EtoAc

Sources & evidence

ORD record
ord-8e5a20f04302476ab98ba1a8e823eb5a
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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