1,1'-Carbonyldiimidazole → HCID 89655861, compound

HRID 2206863Notes

Reaction equation

HRID 2206863 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)\[C:12](=[NH:16])[N:13]([OH:15])[CH3:14])[CH:5]=[CH:4][CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>C(#N)C.CCOC(C)=O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)\[C:12]2[N:13]([CH3:14])[O:15][C:23](=[O:24])[N:16]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 89655955HCID 89655955, compound

Product 1

HCID 89655861HCID 89655861, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2Z)-2-{[(6-bromopyridin-2-yl)methoxy]imino}-N-hydroxy-N-methyl-2-phenylethanimidamide (4.0 g, 11 mmol, 1 eq.) in acetonitrile (100 ml), was added 1,1′-carbonyldiimidazole (2.14 g, 13.2 mmol, 1.2 eq.). After stirring at 80° C. for 1 hours and 2 hours at room temperature, the reaction was diluted with EtOAc (500 mL), subsequently washed with H2O (500 mL) and brine. After separation, the organic phase was dried over MgSO4 then concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(6-bromopyridin-2-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (4.40 g, 95% yield).

Workup

  1. washsubsequently washed with H2O (500 mL) and brine
  2. customAfter separation
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationthen concentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-dd68d6be61cd4e8b9970329d7b0e6edc
Source dataset
uspto-grants-2016_06
Patent number
US09375010B2

Reaction notes

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