Dimethylformamide → ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-4-dimethylaminomethyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionate

HRID 863086

Reaktionsgleichung

Reaktionsgleichung von HRID 863086
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]1=[S:23].[Cl-].CC=[N+]=CC.[CH3:30][N:31]([CH:33]=O)[CH3:32]>>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[C:15]([CH2:30][N:31]([CH3:33])[CH3:32])=[CH:14][N:13]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]1=[S:23]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 19699405ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionateHCID 21873455N,N-dimethylmethylene ammonium chloride

Produkt 1

HCID 19699336ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-4-dimethylaminomethyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionate

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionate (0.5 g, 1.5 mmol), prepared as in Example 34, and N,N-dimethylmethyleneammonium chloride (0.17 g, 1.8 mmol) in 7 mL of DMF was heated at 80° C. under nitrogen for 16 hours. The mixture then was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic layer was separated, washed with brine, dried (NaSO4), filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane to give ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-4-dimethylaminomethyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionate (277 mg, 0.7 mmol), m.p. 128°-130° C.

Aufarbeitung

  1. customThe mixture then was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b4cba53e4cd54a9bb9eaa88ffaaf75c1
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719280

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