Pyridine → HCID 24752077, Verbindung

HRID 252244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252244
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.N1C=CC=CC=1.[O-:18][C:19]#[N:20].[Na+].Cl.[NH2:23][C:24]1[S:25][C:26]([CH3:30])=[C:27]([CH3:29])[N:28]=1>C(#N)C.C(O)(=O)C.O>[CH3:29][C:27]1[N:28]=[C:24]([NH:23][C:19]([NH:20][S:7]([C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([CH3:11])[CH:2]=2)(=[O:9])=[O:8])=[O:18])[S:25][C:26]=1[CH3:30]

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 27345953-Methylbenzenesulphonyl chlorideHCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)

Produkt 1

HCID 24752077HCID 24752077, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

m-Toluenesulfonyl chloride (0.076 ml, 0.53 mmol, 1.4 equiv.) and pyridine (0.103 ml, 1.27 mmol, 3.4 equiv.) were added to a stirred suspension of sodium cyanate (56 mg, 0.86 mmol, 2.3 equiv.) in dry acetonitrile (1 ml) and the mixture stirred at room temperature for 3 hours. 2-Amino-4,5-dimethylthiazole hydrochloride (34 mg, 0.28 mmol, 1.0 equiv.) was added and the reaction stirred for 1 hour. Water (2 ml) and acetic acid (3 drops) were added. The resulting precipitate was centrifuged for 10 minutes and the supernatant decanted. The solid washed with water (2 ml), the material centrifuged and supernatant decanted. The solid was dried under reduced pressure at 40° C. to give N-[(4,5-dimethyl-1,3-thiazol-2-yl)carbamoyl]-3-methylbenzenesulfonamide, 49 mg (55% yield). LC @UV215 nm; Rt 1.81: 93%, m/z (ES+): 326 (MH+), 651 (2 MH+); δH(400 MHz; d4-methanol) 7.54-7.98 (4H, m), 2.57 (3H, s), 2.31 (3H, s), 2.27 (3H, s).

Aufarbeitung

  1. stirringthe reaction stirred for 1 hour
  2. waitThe resulting precipitate was centrifuged for 10 minutes
  3. washThe solid washed with water (2 ml)
  4. customThe solid was dried under reduced pressure at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-207d606a02e34799af541a953586ce46
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868030B2

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