Iodine → HCID 19994945, compound

HRID 2248609Notes

Reaction equation

HRID 2248609 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1([N:18]=[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[N:16][CH:15]=[N:14]1.[I:32]I>O1CCCC1.C(OCC)(=O)C>[C:26]1([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][N:13]2[C:17]([I:32])=[N:16][CH:15]=[N:14]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 807IodineHCID 7912DiisopropylamineHCID 19994944HCID 19994944, compoundHCID 178418339Butyllithium

Product 1

HCID 19994945HCID 19994945, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.3 g (12.8 mmol) of diisopropyl amine in 30 mL is cooled to -78° C. n-Butyllithium (4.3 mL of a 1.6M solution in hexanes, 6.9 mmol) is added dropwise. Over 1/2 h, the solution is warmed to 0° C. and recooled to -78° C. A solution of 2.0 g (6.3 mmol) of N-(1H-1,2,4-triazol-1-yl)-benzophenone imine in 5 mL of tetrahydrofuran is added. The solution is stirred 10 min before 1.7 g (6.7 mmol) of iodine are added. The reaction mixture is warmed to room temperature, diluted with ethyl acetate and washed with saturated aqueous NaHSO3, water and brine. Drying (MgSO4) and removal of solvent gives the desired product.

Workup

  1. additionis added dropwise
  2. customrecooled to -78° C
  3. additionare added
  4. temperatureThe reaction mixture is warmed to room temperature
  5. washwashed with saturated aqueous NaHSO3, water and brine
  6. customDrying
  7. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-568a81db27f0407492d093dd55cac991
Source dataset
uspto-grants-1991_08
Patent number
US05041458

Reaction notes

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