1,1'-Carbonyldiimidazole → HCID 66616156, compound

HRID 2172159Notes

Reaction equation

HRID 2172159 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[C:6]([NH:8][NH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)=[O:7])#[N:2].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].C(OCC)(=O)C.ClCCl>ClC(Cl)C>[C:1]([C:3]1[CH:4]=[C:5]([C:6]2[O:7][C:23](=[O:24])[N:9]([C:10]3[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=3)[N:8]=2)[CH:20]=[CH:21][CH:22]=1)#[N:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 21226138Dichloromethane ethylacetateHCID 66616066HCID 66616066, compound

Product 1

HCID 66616156HCID 66616156, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Methyl 4-[2-(3-cyanobenzoyl)hydrazino]benzoate (0.59 g, 2.0 mmol) and carbonyldiimidazole (0.49 g, 3.0 mmol) are stirred at 80° C. in dichloroethane (20 mL) overnight, and the mixture is then subjected to chromatography directly (silica gel, 1:9 ethyl acetate-dichloromethane) to provide methyl 4-[5-(3-cyanophenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]benzoate (0.63 g, 98%). MS (ES+) m/z: 322.

Sources & evidence

ORD record
ord-682b0fe607ff47faa1720f156fc24fd8
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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