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

HRID 520246

Reaction equation

HRID 520246 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].Cl.Cl[CH2:14][C:15]1[N:16]=[C:17]([NH2:20])[S:18][CH:19]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.CN(C=O)C>[NH2:20][C:17]1[S:18][CH:19]=[C:15]([CH2:14][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:16]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 5464219N-Hydroxybenzimidoyl cyanide

Product 1

HCID 89443882(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]benzenecarboximidoyl cyanideYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (7.3 g, 49.95 mmol, 1 eq.) in 280 ml of acetonitrile and 30 ml of DMF, was added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (11.09 g, 59.94 mmol, 1.2 eq.) followed by potassium iodide (829 mg, 4.99 mmol, 0.1 eq.) and caesium carbonate (39.06 g, 119.88 mmol, 2.4 eq.). The reaction was stirred overnight at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. Ater separation, the organic phase was dried over MgSO4 then concentrated. The residue was purified by chromatography on silica gel to give (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (10.30 g, 80% 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. customAter 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-de8391f389654b3dadd29800fb3952a3
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Linked notes

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