4-Aminobenzoic Acid → 4-[(Cyclohexylcarbonyl)amino]benzoic acid

HRID 2362095Notes

Reaction equation

HRID 2362095 reaction equation
NC1C=CC(C(O)=O)=CC=1.C1(C(Cl)=O)CCCCC1.CCN(CC)CC.[OH-].[Na+].[CH:29]1([C:35]([NH:37][C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44]C)=[O:43])=[CH:40][CH:39]=2)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C1COCC1>[CH:29]1([C:35]([NH:37][C:38]2[CH:47]=[CH:46][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=2)=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

7

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 75938Cyclohexanecarbonyl chlorideHCID 4400321HCID 4400321, compound

Product 1

HCID 7457334-[(Cyclohexylcarbonyl)amino]benzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-aminobenzoic acid 48a (1.98 mmol, 300 mg), cyclohexanecarbonyl chloride 48b (1.98 mmol, 291 mg), and Et3N (2.52 mmol, 0.43 mL) in 6 mL of THF was stirred at room temperature overnight. 1N aqueous NaOH (7.9 mmol, 7.9 mL) was added to the mixture (containing methyl 4-(cyclohexanecarboxamido)benzoate 48c) and the reaction mixture was stirred for 5 h at room temperature. The THF was removed by rotary evaporation and 1N aqueous HCl was added to precipitate the product, which was filtered to give 480 mg (92%) of 48d.

Workup

  1. stirringthe reaction mixture was stirred for 5 h at room temperature
  2. customThe THF was removed by rotary evaporation and 1N aqueous HCl
  3. additionwas added
  4. customto precipitate the product, which
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-5a5064357e3546e181f9ef3e3b391949
Source dataset
uspto-grants-2014_04
Patent number
US08691805B2

Reaction notes

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