Potassium Iodide → (Z)-N-[(2-bromo-1,3-thiazol-4-yl)methoxy]benzenecarboximidoyl cyanide

HRID 2206865Notes

Reaction equation

HRID 2206865 reaction equation
[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)\[C:4]#[N:5].[Br:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18]Br)[N:17]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(#N)C>[Br:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][O:1]/[N:2]=[C:3](/[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)\[C:4]#[N:5])[N:17]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 5464219N-Hydroxybenzimidoyl cyanideHCID 533022182-Bromo-4-(bromomethyl)-1,3-thiazole

Product 1

HCID 89656177(Z)-N-[(2-bromo-1,3-thiazol-4-yl)methoxy]benzenecarboximidoyl cyanideYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of (2Z)-(hydroxyimino)(phenyl)acetonitrile (2.9 g, 19.84 mmol, 1 eq.), 2-bromo-4-(bromomethyl)thiazole (5.10 g, 19.84 mmol, 1 eq.), potassium iodide (329 mg, 1.98 mmol, 0.1 eq.) and caesium carbonate (9.70 g, 29.76 mmol, 1.5 eq.) was added 80 ml of acetonitrile and 10 ml of DMF. The reaction was stirred 2 h at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. After separation, the organic phase was dried over MgSO4 then concentrated. The residue was purified by chromatography on silica gel to give (2Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (5.70 g, 88% yield, only 1 oxime isomer).

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washsubsequently washed with H2O and brine
  4. customAfter separation
  5. dry with materialthe organic phase was dried over MgSO4
  6. concentrationthen concentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8e67e6a4c9be45758b1570752847c98c
Source dataset
uspto-grants-2016_06
Patent number
US09375010B2

Reaction notes

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