Potassium Iodide → HCID 86650760, compound

HRID 875229Notes

Reaction equation

HRID 875229 reaction equation
[OH:1][N:2]=[C:3]([C:9]1[N:13]([CH3:14])[CH:12]=[N:11][CH:10]=1)[C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.Cl.Cl[CH2:17][C:18]1[N:19]=[C:20]([NH2:23])[S:21][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O1CCOCC1>[CH3:14][N:13]1[C:9]([C:3](=[N:2][O:1][CH2:17][C:18]2[N:19]=[C:20]([NH2:23])[S:21][CH:22]=2)[C:4]2[CH:8]=[CH:7][S:6][CH:5]=2)=[CH:10][N:11]=[CH:12]1

Participants

7

Reactant 4

HCID 4875Potassium Iodide2×HCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 86650757HCID 86650757, compound

Product 1

HCID 86650760HCID 86650760, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(3-thienyl)methanimine (4.96 g, 23.9 mmol) and 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (4.88 g, 26.3 mmol) in acetonitrile (50 mL) were added cesium carbonate (13.5 g, 41.4 mmol) and potassium iodide (327 mg, 1.97 mmol). After stirring at room temperature for 51 h, 1,4-dioxane (25 mL) and potassium iodide (5.90 g, 35.5 mmol) were added and the mixture was stirred for 72 h at room temperature then at 70° C. for 3.5 h. The reaction mixture was filtered, the insolubles washed with acetone and methanol, and the filtrate concentrated in vacuo, diluted in ethyl acetate (50 mL), washed with water (2×30 mL), dried over MgSO4 and concentrated to dryness in vacuo. Purification of the residue on silica gel afforded 4-[({[(1-methyl-1H-imidazol-5-yl)(3-thienyl)methylene]amino}oxy)-methyl]-1,3-thiazol-2-amine [850 mg, yield 11%; HPLC/MS: m/z=320 (M+H); log P(HCOOH)=0.45].

Workup

  1. stirringthe mixture was stirred for 72 h at room temperature
  2. waitat 70° C. for 3.5 h
  3. filtrationThe reaction mixture was filtered
  4. washthe insolubles washed with acetone and methanol
  5. concentrationthe filtrate concentrated in vacuo
  6. additiondiluted in ethyl acetate (50 mL)
  7. washwashed with water (2×30 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness in vacuo
  10. customPurification of the residue on silica gel

Sources & evidence

ORD record
ord-c5ab683e698a41d28599af63602fad4c
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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