Potassium Carbonate → HCID 18671679, compound

HRID 1057636Notes

Reaction equation

HRID 1057636 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]([CH3:22])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]#[N:32]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:30][C:31]#[N:32])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([CH3:22])[CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 18671667HCID 18671667, compound

Product 1

HCID 18671679HCID 18671679, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture 9-benzyl-6-methyl-9H-carbazol-4-ol (1.4172 g, 0.0049 mol), potassium carbonate (0.8184 g, 0.0059 mol), bromoacetonitrile (0.75mL, 0.011 mol) and DMF (18 mL) is stirred at room temperature for 3 h. The mixture is then partitioned between water and dichloromethane and the combined organic layers are dried over sodium sulfate and concentrated to a residue. Water is added to the residue and solids precipitated. The solids are collected by filtration and washed with water, followed by a little hexane, and then vacuum dried at room temperature. The solids are chromatographed on silica gel (150 mL) using dichloromethane (100%) to give 1.4723 g (91%) of the title compound. An aliquot is recrystallized from ethyl acetate/hexane, chromatographed on silica gel (50 mL) using ethyl acetate/hexane (20/80) and then recrystallized again from ethyl acetate/dichloromethane/hexane; mp 188-188.25° C.; MS (ESI+) for C22H18N2O m/z 327.2 (M+H)+; IR (drift) 1497, 1467, 1447, 1365, 1340, 1305, 1264, 1237, 1152, 1126, 1053, 799, 781, 754, 711 cm−; 1H NMR (CDCl3) δ2.54, 5.06, 5.49, 6.73, 7.10, 7.25, 7.36, 8.10. Anal. Calcd for C22H18N2O: C, 80.96; H, 5.56; N, 8.58. Found: C, 80.62; H, 5.68; N, 8.55.

Workup

  1. customThe mixture is then partitioned between water and dichloromethane
  2. dry with materialthe combined organic layers are dried over sodium sulfate
  3. concentrationconcentrated to a residue
  4. additionWater is added to the residue and solids
  5. customprecipitated
  6. filtrationThe solids are collected by filtration
  7. washwashed with water
  8. customvacuum dried at room temperature
  9. customThe solids are chromatographed on silica gel (150 mL)

Sources & evidence

ORD record
ord-39a2b0f30774481aa6dd84d721e143be
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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