1,1'-Carbonyldiimidazole → 3-(4-amino-1,2,5-oxadiazol-3-yl)-4-(3-chlorophenyl)-1,2,4-oxadiazol-5(4H)-one

HRID 386811Notes

Reaction equation

HRID 386811 reaction equation
[NH2:1][C:2]1[C:3]([C:7](=[N:16][OH:17])[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[N:4][O:5][N:6]=1.C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1>O1CCCC1.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=3)[C:23](=[O:24])[O:17][N:16]=2)=[N:4][O:5][N:6]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178509308HCID 178509308, compound

Product 1

HCID 585582673-(4-amino-1,2,5-oxadiazol-3-yl)-4-(3-chlorophenyl)-1,2,4-oxadiazol-5(4H)-oneYield 95.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-amino-N-(3-chlorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (540 mg, 2.1 mmol) and N,N-carbonyldiimidazole (380 mg, 2.3 mmol) in tetrahydrofuran (10 mL) was heated at 80° C. for 1 h. The reaction mixture was diluted with ethyl acetate (150 mL) and washed with 0.1 N HCl (3×75 mL) and brine (75 mL). The organic layer was dried with sodium sulfate, filtered, and concentrated to give the desired product (560 mg, 94%) as a white solid which was used without further purification. LCMS for C10H7ClN5O3 (M+H)+: m/z=279.9.

Workup

  1. washwashed with 0.1 N HCl (3×75 mL) and brine (75 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5ff6030dc7ac490da210779f2c11fbf9
Source dataset
uspto-grants-2013_02
Patent number
US08372870B2

Reaction notes

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