4-Aminobenzoic Acid → 4-(Cyclohexanecarboxamido)benzoic acid

HRID 1023101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023101
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

Komponenten

7

Edukt 5

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

Produkt 1

HCID 7457334-(Cyclohexanecarboxamido)benzoic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-074cf85ee75b42dea8efe06ce31abc54
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722658B2

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