Water → HCID 178503420, Verbindung

HRID 1012181

Reaktionsgleichung

Reaktionsgleichung von HRID 1012181
[Zn:1].[CH3:2][S:3][C:4]1[N:9]=[C:8]([C:10]2[S:14][C:13]([S:15](Cl)(=[O:17])=[O:16])=[CH:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1.O>C1COCC1.O>[CH3:2][S:3][C:4]1[N:9]=[C:8]([C:10]2[S:14][C:13]([S:15]([Zn:1])(=[O:17])=[O:16])=[CH:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 23994ZincHCID 27369955-(2-(Methylthio)-4-pyrimidinyl)-2-thiophenesulfonyl chloride

Produkt 1

HCID 178503420HCID 178503420, VerbindungAusbeute 236,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

Zinc dust (106.5 mg, 1.63 mmol) in THF/H2O (2:1, 7.5 mL) was sonicated 15 minutes and 5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophene-2-sulfonyl chloride (500 mg, 1.63 mmol) was added all at once as a solid. After 22 hours, the mixture was concentrated to ¼ volume and a precipitate formed. Water was added and the suspension was sonicated for 1 minute. The solids were collected by filtration, washed with water and dried in vacuo to afford bis-5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophene-2-sulfonyl Zinc as a light yellow solid (1.3 g, >100%). This material was used in the next step. 1H NMR (500 MHz, DMSO-d6) δ 2.52 (s, 3H), 7.15 (d, J=3.5 Hz, 1H), 7.59 (d, J=5.5 Hz, 1H), 7.88 (d, J=3.5 Hz, 1H), 8.54 (d, J=5.5 Hz, 1H).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customa precipitate formed
  3. customthe suspension was sonicated for 1 minute
  4. filtrationThe solids were collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f9a4331eddaf4ce7a1513e59357c3d25
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977481B2

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