Potassium Iodide → 4-[({[(4-Methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino-}oxy)methyl]-1,3-thiazol-2-amine

HRID 875192Notes

Reaction equation

HRID 875192 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[O:14][CH:13]=[N:12][C:11]=1[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.Cl[CH2:18][C:19]1[N:20]=[C:21]([NH2:24])[S:22][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>O1CCOCC1.O>[CH3:15][C:11]1[N:12]=[CH:13][O:14][C:10]=1[C:3](=[N:2][O:1][CH2:18][C:19]1[N:20]=[C:21]([NH2:24])[S:22][CH:23]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 86650729N-hydroxy-1-(4-methyl-1,3-oxazol-5-yl)-1-phenylmethanimine

Product 1

HCID 910959194-[({[(4-Methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino-}oxy)methyl]-1,3-thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-hydroxy-1-(4-methyl-1,3-oxazol-5-yl)-1-phenylmethanimine (0.18 g, 0.89 mmol prepared as described for example 320), dissolved in dioxane (17 mL) were added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (181 mg, 0.98 mmol), cesium carbonate (1.16 g, 3.56 mmol) and potassium iodide (15 mg, 0.9 mmol). After stirring for 48 hours at room temperature water was added and the mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to afford after purification on silica 4-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine (95 mg, 30%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford
  7. customafter purification on silica 4-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine (95 mg, 30%)

Sources & evidence

ORD record
ord-a6f8c3c510834f9aae6b6195afa87f00
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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