Sodium Iodide → HCID 9844278, compound

HRID 1057624Notes

Reaction equation

HRID 1057624 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([Cl:22])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28]Cl)[CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:25][CH2:24][N:26]([CH2:30][CH3:31])[CH2:27][CH3:28])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([Cl:22])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 18671685HCID 18671685, compound

Product 1

HCID 9844278HCID 9844278, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Benzyl-6-chloro-9H-carbazol-4-ol (0.0616 g, 0.20 mmol), 2-diethylaminoethylchloride hydrochloride (0.0517 g, 0.30 mmol), potassium carbonate (0.0863 g, 0.62 mmol), sodium iodide (0.0027 g, 0.018 mmol) and DMF (1 mL) are heated at 85° C. for 3.5 h. After the mixture had cooled, it is partitioned between water and ether. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (60 mL) using methanol/dichloromethane (1/99 to 2/98 to 4/96) to give 0.0665 g (82%) of the title compound; mp 96-97.5° C.; MS (ESI+) for C25H27ClN2O m/z 407.3 (M+H)+; IR (drift) 2966, 1583, 1466, 1453, 1340, 1268, 1242, 1149, 1124, 1069, 795, 780, 745, 718, 708 cm−1; 1H NMR (CDCl3) δ1.16, 2.75, 3.12, 4.34, 5.47, 6.69, 6.97, 7.08, 7.21-7.38, 8.34. Anal. Calcd for C25H27ClN2O: C, 73.79; H, 6.69; N, 6.88. Found: C, 73.39; H, 6.73; N, 6.78.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ether
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (60 mL)

Sources & evidence

ORD record
ord-e3a236d4b1e94e1194fab0a9d5fd8daf
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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