Benzoyl chloride, 3-chloro- → 1-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol
Reaction equation
[OH:1][CH:2]([CH3:7])[C:3]([NH:5][OH:6])=[NH:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](Cl)=O>N1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([C:12]2[O:6][N:5]=[C:3]([CH:2]([OH:1])[CH3:7])[N:4]=2)[CH:15]=[CH:16][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3.19 g (30.6 mmol) 2,N-dihydroxy-propionamidine in 25 ml pyridine was added 4.3 ml (33.7 mmol) 3-chloro-benzoyl chloride at 0° C. Cooling was removed and the mixture was stirred at room temperature for 25 min and at reflux for 25 min. After cooling the mixture was poured into water and extracted twice with CH2Cl2. The organic phase was dried and concentrated. Recrystallization from heptane/EtOAc afforded 4.12 g (60%) of a white solid. 1H NMR (CDCl3), d (ppm): 1.68 (d, 3 H) 2.67 (m, 1 H) 5.09 (m, 1 H) 7.46 (t, 1 H) 7.56 (d, 1 H) 8.01 (d, 1 H) 8.13 (s, 1 H).