Potassium Iodide → HCID 86650745, compound

HRID 875209Notes

Reaction equation

HRID 875209 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=1)[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+]>C(#N)C>[CH3:15][N:14]1[C:10]([C:3](=[N:2][O:1][CH2:18][C:19]2[N:20]=[C:21]([NH2:24])[S:22][CH:23]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:11][N:12]=[CH:13]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 86650744HCID 86650744, compound

Product 1

HCID 86650745HCID 86650745, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-phenylmethanimine (3.90 g, 19.4 mmol) and 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (3.95 g, 21.3 mmol) in acetonitrile (50 mL) were added cesium carbonate (13.3 g, 40.7 mmol) and potassium iodide (322 mg, 1.93 mmol). After stirring at room temperature for 29 h, N-N-dimethylformamide (5 mL) was added and the mixture was further at room temperature for 72 h. The reaction mixture was filtered, the insolubles washed with acetone, and the filtrate concentrated in vacuo. Purification on silica gel afforded 4-[({[(1-methyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine [1.09 g, yield 16%; HPLC/MS: m/z=314 (M+H); log P(HCOOH)=0.69].

Workup

  1. waitthe mixture was further at room temperature for 72 h
  2. filtrationThe reaction mixture was filtered
  3. washthe insolubles washed with acetone
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-733a18a0fe80415fa2d1e98abe7d5bb6
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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