Dicyclohexylcarbodiimide → Dimethyl 2-((2,4-dichlorophenyl)acetylamino)terephthalate

HRID 1072856

Reaktionsgleichung

Reaktionsgleichung von HRID 1072856
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[CH2:24][C:25](O)=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[CH2:24][C:25]([NH:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:26]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 79336Dimethyl aminoterephthalateHCID 882092,4-Dichlorophenylacetic acid

Produkt 1

HCID 22388140Dimethyl 2-((2,4-dichlorophenyl)acetylamino)terephthalateAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of dimethyl 2-aminoterephthalate (2.09 g), 2,4-dichlorophenylacetic acid (2.05 g), N,N-dimethylaminopyridine (1.32 g) and dicyclohexylcarbodiimide (2.22 g) in tetrahydrofuran (20 ml) was stirred at room temperature for 2 hr and then at 80° C. for 4 hr. After cooling, the precipitate was filtered off and the filtrate was washed with 1N hydrochloric acid. Chloroform was added to the obtained organic layer, and the mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and dried over sodium sulfate. The solvent was distilled away and the residue was washed with water and methanol to give the object compound (2.54 g) as white crystals.

Aufarbeitung

  1. waitat 80° C. for 4 hr
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. washthe filtrate was washed with 1N hydrochloric acid
  5. additionChloroform was added to the obtained organic layer
  6. washthe mixture was washed with a saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialdried over sodium sulfate
  8. distillationThe solvent was distilled away
  9. washthe residue was washed with water and methanol

Quellen und Nachweise

ORD-Eintrag
ord-499bc9d95dd44215910bff302cfe4c5b
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911469B2

Verknüpfte Notizen

Wird geladen…