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

HRID 1258593Notes

Reaction equation

HRID 1258593 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16][CH3:17])[CH:11]=1)[C:4]1[N:8]([CH3:9])[N:7]=[N:6][N:5]=1.Cl[CH2:19][C:20]1[N:21]=[C:22]([NH2:25])[S:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH3:17][S:16][C:12]1[CH:11]=[C:10]([C:3](=[N:2][O:1][CH2:19][C:20]2[N:21]=[C:22]([NH2:25])[S:23][CH:24]=2)[C:4]2[N:8]([CH3:9])[N:7]=[N:6][N:5]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 732294-Chloromethylthiazol-2-ylamineHCID 136352704N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

Product 1

HCID 866531454-{[({[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}-1,3-thiazol-2-amineYield 44.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine (2.00 g, 6.90 mmol), in dry acetonitrile (115 mL) were added 4-(chloromethyl)-1,3-thiazol-2-amine (1.13 g, 7.59 mmol), cesium carbonate (4.72 g, 14.5 mmol) and potassium iodide (0.57 g, 3.45 mmol). The reaction mixture was stirred at room temperature for 26 h, then insolubles were removed by filtration and washed with dichloromethane (3×40 mL) and ethyl acetate (3×40 mL). The filtrates were combined and concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL), washed with water (50 mL), the aqueous layer was extracted with dichloromethane (50 mL) and the combined organic layers were dried over MgSO4 and concentrated in vacuo to afford 4-{[({[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}-1,3-thiazol-2-amine [1.10 g, yield 42%; HPLC/MS: m/z=362 (M+H); logP(HCOOH)=1.76].

Workup

  1. custominsolubles were removed by filtration
  2. washwashed with dichloromethane (3×40 mL) and ethyl acetate (3×40 mL)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  5. washwashed with water (50 mL)
  6. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
  7. dry with materialthe combined organic layers were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d300f66efe734e3f93a6b5bc91f3ac76
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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