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

HRID 1528341Notes

Reaction equation

HRID 1528341 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 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (2.5 g, 17.10 mmol, 1 eq.) in 100 ml of acetonitrile and 10 ml DMF was added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (3.79 g, 20.52 mmol, 1.2 eq.) followed by potassium iodide (283 mg, 1.71 mmol, 0.1 eq.) and caesium carbonate (13.37 g, 41.05 mmol, 2.4 eq.). The reaction was stirred overnight at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc (100 ml). The organic layer was washed with H2O and dried over MgSO4 then concentrated. (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (4 g, 90% yield, only 1 oxime isomer) was obtained as a white solid.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue dissolved in EtOAc (100 ml)
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-b941f558737340e3a36bf5c68caf4ba2
Source dataset
uspto-grants-2015_07
Patent number
US09090600B2

Reaction notes

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