Iodine → HCID 19022650, compound

HRID 1034451Notes

Reaction equation

HRID 1034451 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[NH:12][C:11](=[O:20])[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.C[Si]([I:32])(C)C.II>C(Cl)Cl>[I:32][CH:10]1[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[NH:12][C:11]1=[O:20]

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 85247Trimethylsilyl iodideHCID 19022613HCID 19022613, compound

Product 1

HCID 19022650HCID 19022650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (-20° C.) solution of 500mg (1.87mmole) of 2,3,4,5-tetrahydro-4-(4-methoxyphenyl)-1H-1-benzazepin-2-one in 10 mL of methylene chloride was added triethylamine (1.04g, 9.35 mmol, 5eq.) followed by trimethylsilyl iodide (749mg, 3.74mmol, 2eq.). After 15 minutes, 950 mg (3,74 mmol, 2eq) of iodine was added and the brown mixture was stirred at 0° C. for one hour. The reaction mixture was diluted with methylene chloride, washed with aqueous sodium bisulfite solution, water and brine and then dried (MgSO4). Filtration followed by evaporation of the solvent under vacuum gave the product as a mixture of cis and trans isomers (675 mg,92%). FAB-MS: calculated for C17H16NO2I 393; found 393 (100%), 394 (20%).

Workup

  1. washwashed with aqueous sodium bisulfite solution, water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationFiltration
  4. customfollowed by evaporation of the solvent under vacuum
  5. customgave the product
  6. additionas a mixture of cis and trans isomers (675 mg,92%)

Sources & evidence

ORD record
ord-be2a2c8471b444d08b267c0adfd561dc
Source dataset
uspto-grants-1994_05
Patent number
US05317017

Reaction notes

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