Dicyclohexylcarbodiimide → 2-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide

HRID 2103084

Reaktionsgleichung

Reaktionsgleichung von HRID 2103084
[C:1]1(=[CH:5][C:6]([OH:8])=O)[CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]1[C:11]([O:18][CH3:19])=[CH:12][CH:13]=[C:14]([C:16]=1[CH3:17])[NH2:15].CN(C)CCCN=C=NCC.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl.C(N(CC)CC)C>[C:1]1(=[CH:5][C:6]([NH:15][C:14]2[CH:13]=[CH:12][C:11]([O:18][CH3:19])=[C:10]([CH3:9])[C:16]=2[CH3:17])=[O:8])[CH2:2][CH2:3][CH2:4]1

Komponenten

8

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 110948094-Methoxy-2,3-dimethylanilineHCID 219231732-Cyclobutylideneacetic acid

Produkt 1

HCID 690533272-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamideAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Cyclobutylideneacetic acid (3.8 g), 5,6-dimethyl-4-methoxyaniline (5 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) (4.7 g), 1,3-dicyclohexylcarbodiimide (DCC) (2.4 g), 4-dimethylaminopyridine (DMAP) (805 mg) and triethylamine (TEA) (7.3 g) were dissolved in dichloromethane (80 mL). The mixture was stirred at room temperature overnight, concentrated, and the residue dissolved in ethyl acetate. The organic phase was washed with water (3×20 mL) and 1M HCl (3×20 mL), and a white solid was filtered out. The organic solution was then dried out by evaporation giving 2-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide as a brown solid (5.3 g). The product was used in the next step without further purification. MS: (m/z)=246 (100, M+H+).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic phase was washed with water (3×20 mL) and 1M HCl (3×20 mL)
  4. filtrationa white solid was filtered out
  5. customThe organic solution was then dried out by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e76f5d88b4074044a32e6ad90da2d763
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576094B2

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