Nitrogen → HCID 66928550, Verbindung

HRID 42810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42810
N#N.[CH3:3][C:4]1([C:9]2[S:13][CH:12]=[C:11]([CH2:14]O)[CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.S([Cl:27])(C)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:27][CH2:14][C:11]1[CH:10]=[C:9]([C:4]2([CH3:3])[O:8][CH2:7][CH2:6][O:5]2)[S:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66928500HCID 66928500, Verbindung

Produkt 1

HCID 66928550HCID 66928550, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-3-yl]-methanol (460 mg, 2.30 mmol) in dry CH2Cl2 (4.6 mL) was treated at 0° C. with Et3N (0.42 mL, 2.99 mmol) followed by DMAP (28 mg, 0.23 mmol) and Ms-Cl (0.21 mL, 2.76 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (20 mL) and the combined org. extracts were dried over NaSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a pale yellow oil. TLC:rf (1:4 EA-Hept)=0.35.

Aufarbeitung

  1. customthe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with CH2Cl2 (20 mL)
  3. dry with materialextracts were dried over NaSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (4:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-efc475add29548edbd361e787547b8d9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536209B2

Notizen zur Reaktion

Wird geladen…