3-Bromofuran-2-carbonyl chloride → 3-(3-Amino-4-chloro-phenyl)-5-(3-bromofuran-2-yl)-[1,2,4]-oxadiazole

HRID 856971Notes

Reaction equation

HRID 856971 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5](=[N:7][OH:8])[NH2:6].[Br:13][C:14]1[CH:18]=[CH:17][O:16][C:15]=1[C:19](Cl)=O>N1C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:19]([C:15]3[O:16][CH:17]=[CH:18][C:14]=3[Br:13])[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

4

Reactant 2

HCID 218645763-Bromofuran-2-carbonyl chlorideHCID 738515633-Amino-4-chloro-benzamidoxime

Product 1

HCID 162223973-(3-Amino-4-chloro-phenyl)-5-(3-bromofuran-2-yl)-[1,2,4]-oxadiazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound was prepared from 3-amino-4-chloro-benzamidoxime (293 mg, 1.58 mmol) and 3-bromofuran-2-carbonyl chloride (329 mg, 1.57 mmol) in pyridine (2.8 mL) under reflux similar to Example 1b, yielded 289 mg (54%) as a white solid. 1H NMR (CDCl3): 7.66 (d, J=1.64 Hz, 1H), 7.59 (d, J=1.92 Hz, 1H), 7.50 (dd, J1=8.38 Hz, J2=2.07 Hz, 1H), 7.37 (d, J=8.24 Hz, 1H), 6.75 (d, J=1.93 Hz, 1H), 4.22 (s, 2H).

Workup

  1. temperatureunder reflux similar to Example 1b
  2. customyielded 289 mg (54%) as a white solid

Sources & evidence

ORD record
ord-d49feab61b7c437a94ab600c7a4fc3dc
Source dataset
uspto-grants-2006_12
Patent number
US07144876B2

Reaction notes

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