Sodium Iodide → HCID 9954320, compound

HRID 585458Notes

Reaction equation

HRID 585458 reaction equation
[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16]([O:23][CH2:24][CH2:25][CH2:26][CH2:27]Cl)=[CH:17][CH:18]=[CH:19][C:20]=53)=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36].[I-].[Na+]>CN(C=O)C>[CH2:35]([N:37]([CH2:38][CH3:39])[CH2:27][CH2:26][CH2:25][CH2:24][O:23][C:16]1[C:15]2[C:14]3[C:22]4=[C:10]([O:9][CH2:8][CH:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[N:21]4[C:20]=2[CH:19]=[CH:18][CH:17]=1)[CH:11]=[CH:12][CH:13]=3)[CH3:36]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 12148637HCID 12148637, compound

Product 1

HCID 9954320HCID 9954320, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-chlorobutyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether (0.36 g, 0.9 mmol) in dry DMF (10 mL) is added potassium carbonate (0.63 g, 4.6 mmol), diethylamine (0.48 mL, 4.6 mmol), and sodium iodide (0.135 g, 0.9 mmol). The mixture is heated at 50° C. for 20 h. The mixture is then cooled to room temperature and partitioned between water and ether. The ether layer is washed twice with water (50 mL) then dried over anhydrous sodium sulfate and concentrated. Column chromatography (60 mL silica) using 5% methanol in methylene chloride as eluent gave 0.127 g (33%) of the title compound.

Workup

  1. temperatureThe mixture is then cooled to room temperature
  2. custompartitioned between water and ether
  3. washThe ether layer is washed twice with water (50 mL)
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-642f0281c5864faeb159459bd562292b
Source dataset
uspto-grants-2005_08
Patent number
US06932961B1

Reaction notes

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