Reaktion #1543124

Reaktionsgleichung

2-benzyloxy-5-bromobenzaldehyde

2-amino-N-propyl-1,3,4-thiadiazole-5-carboxamide

→

2-[N-(2-benzyloxy-5-bromobenzyl)amino]-N-propyl-1,3,4-thiadiazole-5-carboxamide

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 2 hours
3. 3
   SonstigeThe solvent was evaporated
4. 4
   workup.DISSOLUTIONresidue was dissolved in ethanol (100 mL)
5. 5
   Temperaturwas heated
6. 6
   Temperaturunder reflux for 3 hours
7. 7
   workup.ADDITIONSodium borohydride (0.53 g) was added
8. 8
   workup.ADDITIONthen poured into water (500 mL)
9. 9
   ExtraktionThe aqueous mixture was extracted 4 times with ethyl acetate (50 mL each time)
10. 10
    Waschenthe combined extracts were washed 3 times with water (100 mL each time)
11. 11
    Trocknendried (MgSO4)
12. 12
    SonstigeThe residue obtained on removal of the solvent
13. 13
    Wascheneluting with a mixture of ethyl acetate and dichloromethane (1/5 v/v)

Vorschrift

A mixture of 2-benzyloxy-5-bromobenzaldehyde (4.2 g) and 2-amino-N-propyl-1,3,4-thiadiazole-5-carboxamide (2.7 g) in toluene (200 mL) was heated under reflux for 2 hours. The solvent was evaporated and residue was dissolved in ethanol (100 mL) and was heated under reflux for 3 hours then allowed to cool to ambient temperature. Sodium borohydride (0.53 g) was added and the reaction mixture was stirred for 16 hours then poured into water (500 mL). The aqueous mixture was extracted 4 times with ethyl acetate (50 mL each time), the combined extracts were washed 3 times with water (100 mL each time) and dried (MgSO4). The residue obtained on removal of the solvent was subjected to chromatography on silica, eluting with a mixture of ethyl acetate and dichloromethane (1/5 v/v), to give 2-[N-(2-benzyloxy-5-bromobenzyl)amino]-N-propyl-1,3,4-thiadiazole-5-carboxamide, yield 0.81 g, mp 154° C.

Quelle