Triethylamine → n-(4-Methoxyphenyl)-2-(4-tert-butylbenzoyloxy)benzamide

HRID 427654Notes

Reaction equation

HRID 427654 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:26]([C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][C:30]([C:26]([CH3:28])([CH3:27])[CH3:29])=[CH:31][CH:32]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 478806N-(4-Methoxyphenyl)-2-hydroxybenzamide

Product 1

HCID 18174417n-(4-Methoxyphenyl)-2-(4-tert-butylbenzoyloxy)benzamideYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(4-methoxyphenyl)-2-hydroxybenzamide (0.484 g, 2.00 mmol) in methylene chloride (35 mL) cooled to 0° C. was added 0.28 mL triethylamine (0.28 mL, 2.0 mmol), followed by the dropwise addition of a solution of 4-tert-butylbenzoyl chloride (0.393 mL, 2.00 mmol) in methylene chloride (15 mL). The reaction mixture was allowed to warm to room temperature over 16 h and washed with cold water. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Trituration with hexane provided 0.488 g (61%) of the title compound.

Workup

  1. washwashed with cold water
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d68e6b8ab8f45a9b1fa7d5183e1ca76
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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