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Methyl iodide → n-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-n-methylmethanesulfonamide

HRID 567067
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 567067
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CC(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[N:21]([CH3:28])[S:22]([CH3:25])(=[O:23])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 212645206-Benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman

Produkt 1

HCID 21264508n-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-n-methylmethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

8.9 g (25 mmol) of 6-benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman (Ex. 1 e) were introduced in portions at 10° C. into a suspension of 1.2 g (30 mmol) of sodium hydride (60 percent dispersion) in 75 ml of DMA. After stirring at RT for 2 h, 1.9 ml (30 mmol) of methyl iodide were added dropwise, the temperature rising to 50° C. The mixture was then heated to 50° C. for 2 h, concentrated in vac., the residue was treated with water, the resinous product was taken up with EA, the solution was dried and concentrated, and the residue was chromatographed on silica gel using n-heptane/EA (2:1). 7.4 g of product were crystallized from appropriate fractions using petroleum ethendusopropyl ether (1:1), m.p. 114-116° C.

Aufarbeitung

  1. customrising to 50° C
  2. temperatureThe mixture was then heated to 50° C. for 2 h
  3. concentrationconcentrated in vac
  4. addition, the residue was treated with water
  5. customthe solution was dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed on silica gel
  8. custom7.4 g of product were crystallized from appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-0eb8399ccab945c39d4134aaa24a5e2d
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06177449B1

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