Sodium Hydroxide → HCID 66974219, compound

HRID 559599Notes

Reaction equation

HRID 559599 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([S:17][CH3:18])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH:9]=1)=[N+]=[N-].O.O.[Sn](Cl)Cl.[OH-].[Na+]>CCOC(C)=O>[I:16][C:13]1[CH:14]=[CH:15][C:10]([N:8]2[CH:9]=[C:5]([CH2:4][NH2:1])[N:6]=[C:7]2[S:17][CH3:18])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 86616336HCID 86616336, compound

Product 1

HCID 66974219HCID 66974219, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(azidomethyl)-1-(4-iodophenyl)-2-(methylthio)-1H-imidazole (0.26 g, 0.70 mmol) in EtOAc (10 mL), Tin(II) chloride dihydrate (0.63 g, 2.8 mmol) was added. The mixture was heated at reflux for 10 min. After being cooled down, 1N NaOH (10 mL) was added. The white precipitate was filtered off through celite. The EtOAc phase was separated, dried over Na2SO4, concentrated in vacuo to give (1-(4-iodophenyl)-2-(methylthio)-1H-imidazol-4-yl)methanamine (127 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 min
  3. temperatureAfter being cooled down
  4. filtrationThe white precipitate was filtered off through celite
  5. customThe EtOAc phase was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-adb989e86b9b4073916c5c0f8ddfaa22
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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