1,2-Dichloroethane → 4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzenesulfonamide

HRID 1172943Notes

Reaction equation

[S:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].C(Cl)CCl.C1C=C2N=NN(O)C2=CC=1.O.[Cl:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=1[O:40][CH:41]([CH3:43])[CH3:42])/[C:33](=[N:35]/O)/[NH2:34]>CN(C=O)C>[Cl:29][C:30]1[CH:31]=[C:32]([C:33]2[N:35]=[C:9]([C:8]3[CH:7]=[CH:6][C:5]([S:1]([NH2:2])(=[O:3])=[O:4])=[CH:13][CH:12]=3)[O:11][N:34]=2)[CH:37]=[CH:38][C:39]=1[O:40][CH:41]([CH3:43])[CH3:42]

Participants

Conditions

Temperature: 140 °C

Procedure

To a slurry of 4-sulfamoylbenzoic acid (1.452 g, 7.22 mmol) in DMF (8.20 ml) was added EDC (1.383 g, 7.22 mmol) followed by HOBT hydrate (0.975 g, 7.22 mmol). After about 30 minutes a solution of (Z)-3-chloro-N′-hydroxy-4-isopropoxybenzimidamide in DMF (8.20 ml) was added. 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 purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide 4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzenesulfonamide (1.28 g, 50%) as a colorless solid. LCMS (Table 1, Method c) Rt=2.74 min, m/z 392 (M−H)−.

Workup

temperatureAfter cooling to room temperature the reaction mixture
concentrationwas concentrated in vacuo
custompurified
customby purified by chromatography on silica gel (eluting with EtOAc/Hep)

Sources & evidence

ORD record: ord-0bfad23297c4436bbdaadc00bf90b0a9
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834039B2

Reaction notes

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