3-(Methylthio)propionyl Chloride → HCID 59580749, Verbindung

HRID 1803425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803425
[CH3:1][S:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[CH3:8][NH:9][C:10]1[S:14][C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:12][CH:11]=1>ClCCCl.CN(C1C=CN=CC=1)C>[CH3:8][N:9]([C:10]1[S:14][C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:12][CH:11]=1)[C:5](=[O:6])[CH2:4][CH2:3][S:2][CH3:1]

Komponenten

5

Edukt 2

HCID 129214403-(Methylthio)propionyl ChlorideHCID 59580894N-methyl-2-(pyridin-3-yl)thiazol-5-amine

Produkt 1

HCID 59580749HCID 59580749, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 111,2-DichloroethaneLösungsmittel3×

Versuchsvorschrift

A solution of 3-methylsulfanyl-propionyl chloride (120 mg, 0.9 mmol) in DCE (1 mL) was pipetted at a dropwise rate into an ice-cold suspension of methyl-(2-pyridin-3-yl-thiazol-5-yl)-amine (114 mg, 0.6 mmol) in DCE (5 mL), and the mixture was stirred for 5 min before adding a solution of DMAP (80 mg, 0.6 mmol) in DCE (1 mL). The ice bath was removed after 30 min, and the mixture was stirred at reflux under nitrogen for 15 min. The reaction mixture was cooled, diluted with DCE (70 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over MgSO4 and purified by silica gel chromatography (3:1 ethyl acetate/hexanes) to afford a fine yellow powder (131 mg, 75%): mp 116-118° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.08 (d, J=2.0 Hz, 1H), 8.61 (dd, J=4.8, 1.4 Hz, 1H), 8.24 (dt, J=9.8, 1.8 Hz, 1H), 7.81 (s, 1H), 7.51 (dd, J=7.7, 4.7 Hz, 1H), 3.56 (s, 3H), 3.02 (t, J=7.0 Hz, 2H), 2.76 (t, J=7.2 Hz, 2H), 2.12 (s, 3H); ESIMS m/z 294 (M+1).

Aufarbeitung

  1. customThe ice bath was removed after 30 min
  2. stirringthe mixture was stirred
  3. temperatureat reflux under nitrogen for 15 min
  4. temperatureThe reaction mixture was cooled
  5. additiondiluted with DCE (70 mL)
  6. washwashed with saturated aqueous NaHCO3 (50 mL)
  7. dry with materialdried over MgSO4
  8. custompurified by silica gel chromatography (3:1 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3efa78839d344196a623257c3bbb0d53
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08350044B2

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