Reaktion #74595

Reaktionsgleichung

2-amino-1,3,4-thiadiazole

2,4-dimethoxy-benzaldehyde

sodium triacetoxyborohydride

→

title compound

Ausbeute 45.0%

N-(2,4-Dimethoxybenzyl)-1,3,4-thiadiazol-2-amine

Ausbeute 45.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 24 hours
2. 2
   SonstigeThe reaction was quenched with saturated aqueous sodium bicarbonate solution
3. 3
   Extraktionextracted with dichloromethane
4. 4
   TrocknenThe combined organic extracts were dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by flash column chromatography
8. 8
   Wascheneluting with methanol

Vorschrift

To a solution of 2-amino-1,3,4-thiadiazole (3.05 g, 0.0302 mol) and 2,4-dimethoxy-benzaldehyde (4.55 g, 0.0274 mol) in dichloromethane (125 mL) was added chlorotriisopropoxytitanium (16 mL, 0.067 mol) portionwise over 5 minutes. After stirring for 1 hour, sodium triacetoxyborohydride (11.72 g, 0.05530 mol) was added portion wise and stirred for 24 hours. The reaction was quenched with saturated aqueous sodium bicarbonate solution and adjusted to pH 9 with sodium hydroxide (6 N aqueous solution) and extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with methanol:dichloromethane (gradient 0:1 to 1:9, by volume) to afford the title compound as a white solid, 590 mg, 45% yield.

Quelle