4-tert-Butylbenzoyl chloride → Methyl 4-amino-3-[(4-tert-butylbenzoyl)amino]benzoate

HRID 395799Notes

Reaction equation

HRID 395799 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1[NH2:27])[C:20]([O:22][CH3:23])=[O:21]>>[NH2:27][C:26]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[NH:16][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 743724-tert-Butylbenzoyl chlorideHCID 18174510Methyl 3,4-diaminobenzoate dihydrochloride

Product 1

HCID 10687588Methyl 4-amino-3-[(4-tert-butylbenzoyl)amino]benzoateYield 44%

Procedure

Using the procedure described in Example 146, Part A, 4-tert-butylbenzoyl chloride (6.00 mmol) was reacted with methyl 3,4-diaminobenzoate dihydrochloride. As the product did not precipitate directly, the reaction mixture was concentrated in vacuo, diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate solution. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo to provide 0.885 g (44%) of the title compound as a crystalline solid.

Workup

  1. customAs the product did not precipitate directly
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8784a4a9d51847238a9cfb01b2e59f79
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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