4-Methylmorpholine → n,n-Di-n-pentyl-2-methoxy-5-formylbenzamide

HRID 1583030

Reaktionsgleichung

Reaktionsgleichung von HRID 1583030
[CH2:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][C:15]=1[C:16]([OH:18])=O.ON1C2N=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH2:7]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:16](=[O:18])[C:15]1[CH:19]=[C:20]([CH:23]=[O:24])[CH:21]=[CH:22][C:14]=1[O:13][CH3:12])[CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 16316DipentylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 39266835-Formyl-2-methoxybenzoic acid

Produkt 1

HCID 22716819n,n-Di-n-pentyl-2-methoxy-5-formylbenzamideAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Di-n-pentylamine (873 mg, 5.55 mmol, 2 eq) was added to a solution of 2-methoxy-5-formylbenzoic acid (500 mg, 2.78 mmol, 1 eq), 1-hydroxy-7-azabenzotriazole (755 mg, 5.55 mmol, 2 eq), and N-methylmorpholine (0.83 mL, 7.58 mmol, 2.73 eq) in N,N-dimethylformamide (10 mL). To this was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.06 g, 5.55 mmol, 2 eq) and the reaction mixture stirred overnight. The reaction mixture was diluted with ethyl acetate (20 mL) and washed sequentially with 10% HCl (3×20 mL), brine (20 mL), saturated aqueous sodium bicarbonate (2×20 mL) and brine (20 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to give the product as a pale brown oil (886 mg, 99%). 1H NMR (CDCl3) δ9.83 (s, 1H, O═C—H), 3.85 (s, 3H, OCH3), 3.52 (m, 1H, NCH2), 3.38 (m, 1H, NCH2), 2.98 (m, 2H, NCH2).

Aufarbeitung

  1. washwashed sequentially with 10% HCl (3×20 mL), brine (20 mL), saturated aqueous sodium bicarbonate (2×20 mL) and brine (20 mL)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-49f92be5173f42138ec1ae5aee200f28
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740670B2

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