Pyridine → Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl ester

HRID 1921249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921249
[F:1][C:2]1[C:7]2[S:8][CH2:9][CH:10]([NH:11][C:12]([NH:14][CH2:15][CH2:16][OH:17])=[S:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[C:7]2[S:8][CH2:9][CH:10]([NH:11][C:12](=[S:13])[NH:14][CH2:15][CH2:16][O:17][C:24](=[O:26])[CH3:25])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 25135276HCID 25135276, Verbindung

Produkt 1

HCID 25134381Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl esterAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(7-Fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)-3-(2-hydroxy-ethyl)-thiourea (200 mg, 0.73 mmol), pyridine (0.07 mL, 0.88 mmol) and DMAP (20 mg, 0.16 mmol) in THF (5 mL) was added a solution of acetyl chloride (0.06 mL, 0.81 mmol) in THF (2 mL) and the reaction mixture stirred for 16 h. The mixture was diluted with ethyl acetate (20 mL) and extracted with water (4 times). The organic phase was dried over Na2SO4, solvents evaporated and the residue purified by column chromatography to yield Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl ester (125 mg, 0.40 mmol, 54%).

Aufarbeitung

  1. extractionextracted with water (4 times)
  2. dry with materialThe organic phase was dried over Na2SO4, solvents
  3. customevaporated
  4. customthe residue purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-216c90bd23c54ded9c113afac5dc9ad8
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173675B2

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