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

HRID 520250

Reaction equation

HRID 520250 reaction equation
[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)\[C:4]#[N:5].Cl.Cl[CH2:16][C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.CN(C=O)C>[NH2:22][C:19]1[S:20][CH:21]=[C:17]([CH2:16][O:1]/[N:2]=[C:3](/[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)\[C:4]#[N:5])[N:18]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 23502058(2Z)-2-hydroxyimino-2-(3-methoxyphenyl)acetonitrile

Product 1

HCID 89655523(1Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-3-methoxybenzenecarboximidoyl cyanideYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (2Z)-(hydroxyimino)(3-methoxyphenyl)acetonitrile (2.57 g, 14.59 mmol, 1 eq.) in 70 ml of acetonitrile and 7 ml of DMF, was added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (2.87 g, 16.05 mmol, 1.1 eq.) followed by potassium iodide (242 mg, 1.46 mmol, 0.1 eq.) and caesium carbonate (10.45 g, 32.09 mmol, 2.2 eq.). The reaction was stirred 8 h 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 to afford (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(3-methoxyphenyl)acetonitrile (4.03 g, 91% yield, only 1 oxime isomer) which was used in the next step without further purification.

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

Sources & evidence

ORD record
ord-73f9cf3e77cd426a99ba1934ab3f33f5
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Linked notes

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