Acetic Acid → HCID 13576467, Verbindung

HRID 225903

Reaktionsgleichung

Reaktionsgleichung von HRID 225903
CN.CO.[S:5]1[CH:9]=[C:8]([CH:10]=O)[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]1=2.CC(O)=O.[BH3-][C:21]#[N:22].[Na+]>>[CH3:21][NH:22][CH2:10][C:8]1[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[S:5][CH:9]=1

Komponenten

6

Edukt 5

HCID 176Acetic AcidHCID 887MethanolHCID 6329MethylamineHCID 2273281-Benzothiophene-3-carbaldehydeHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 13576467HCID 13576467, VerbindungAusbeute 48 %

Versuchsvorschrift

To a stirred solution of 2 M methylamine in methanol (75 mmole, 150 mmole) was added benzo[b]thiophen-3-carboxaldehyde (5.3 g, 33 mmole) and HOAc (43 mL, 75 mmole). The reaction was stirred at RT for 1 h, then NaBH3CN (2.1 g, 33 mmole) was added portionwise over 5 minutes. The reaction was stirred for an additional 16 b then was concentrated under vacuum. The residue was taken up in Et2O (300 mL) and washed with 1.0 N NaOH (300 mL) then with brine, dried (Na2SO4), and concentrated. Purification by flash chromatography on silica gel (5% (5% NH4OH/MeOH)/CHCl3) gave the title compound (2.81 g, 48%) as a brownish oil: 1H NMR (400 MHz, CDCl3) δ•7.87 (2d, 2 H), 7.40 (m, 2 H), 7.32 (s, 1 H), 4.02 (s, 2 H), 2.56 (s, 3 H), 1.5 (br s, 1 H).

Aufarbeitung

  1. stirringThe reaction was stirred for an additional 16 b
  2. concentrationthen was concentrated under vacuum
  3. washwashed with 1.0 N NaOH (300 mL)
  4. dry with materialwith brine, dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (5% (5% NH4OH/MeOH)/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-c9d59e2993104c6f9f2a46ea2a895260
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557125B2

Verknüpfte Notizen

Wird geladen…