1,1'-Carbonyldiimidazole → HCID 71627024, compound

HRID 520254Notes

Reaction equation

HRID 520254 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)\[C:11](=[NH:15])[N:12]([OH:14])[CH3:13])[N:6]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>C(#N)C>[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)\[C:11]2[N:12]([CH3:13])[O:14][C:22](=[O:23])[N:15]=2)[N:6]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 71626942HCID 71626942, compound

Product 1

HCID 71627024HCID 71627024, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2Z)-2-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-phenylethanimidamide (1.8 g, 4.87 mmol, 1 eq.) in acetonitrile (120 ml), was added 1,1′-carbonyldiimidazole (1.58 g, 9.75 mmol, 2 eq.). After stirring at 80° C. for 1 hour, the reaction was quenched by addition of water (100 ml) and extracted with EtOAc (2×100 ml). The organics were combined, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (2 g, 100% yield).

Workup

  1. customthe reaction was quenched by addition of water (100 ml)
  2. extractionextracted with EtOAc (2×100 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3d720effa36c447cb67946fef7771c95
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Reaction notes

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