1,2-Dichloroethane → (4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanol
Reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C(Cl)CCl.C1C=C2N=NN(O)C2=CC=1.O.[Cl:27][C:28]1[CH:29]=[C:30]([CH:35]=[CH:36][C:37]=1[O:38][CH:39]([CH3:41])[CH3:40])/[C:31](=[N:33]/O)/[NH2:32]>CN(C=O)C>[Cl:27][C:28]1[CH:29]=[C:30]([C:31]2[N:33]=[C:7]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:11][CH:10]=3)[O:9][N:32]=2)[CH:35]=[CH:36][C:37]=1[O:38][CH:39]([CH3:41])[CH3:40]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a slurry of 4-(hydroxymethyl)benzoic acid (0.220 g, 1.443 mmol) in DMF (1.640 ml) was added EDC (0.277 g, 1.443 mmol) followed by HOBT hydrate (0.195 g, 1.443 mmol). After about 45 min. a solution of (Z)-3-chloro-N′-hydroxy-4-isopropoxybenzimidamide (0.300 g, 1.31 mmol) in DMF (1.640 ml) was added and the reaction mixture was heated to about 140° C. for about 2 h. After cooling to room temperature the reaction mixture was concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide (4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanol (0.336 g, 71%) as an off-white solid. LCMS (Table 1, Method c) Rt=2.80 min, m/z 345 (M+H)+.
Workup
- temperatureAfter cooling to room temperature the reaction mixture
- concentrationwas concentrated in vacuo
- custompurified by chromatography on silica gel (eluting with EtOAc/Hep)
Sources & evidence
- ORD record
- ord-cc27233ad9774c00a5b62dd9bfcf4e1e
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834039B2
Reaction notes
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