Carbazole → HCID 68283147, compound

HRID 1293451Notes

Reaction equation

HRID 1293451 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>C(Cl)(Cl)Cl.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

5

Reactant 2

HCID 6854CarbazoleHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 68283147HCID 68283147, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 6212ChloroformSolvent3×

Procedure

To a stirred solution of carbazole (20.0 gm, 0.119 moles) in dry chloroform (300 ml) at 0° C., D-10 camphor sulphonic acid (5% W/W, 1.0 gm) was added followed by a solution of 3,4-dihydro 2H-pyran (0.149 moles, 13.6 ml) in dry chloroform (50 ml) dropwise over a period of 30 min. The reaction mixture was gradually warmed to room temperature and stirred at the same temperature for 2 hours. The reaction mixture was diluted with chloroform (400 ml) and washed with a solution of saturated NaHCO3 (150 ml), followed by water (150 ml), dried over Na2SO4 and concentrated to give 31 gm of crude material which was recrystallised from 500 ml of iso-propanol to give 24 gm of the title product as white crystalline powder, m. p: 131-133° C.

Workup

  1. washwashed with a solution of saturated NaHCO3 (150 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give 31 gm of crude material which
  5. customwas recrystallised from 500 ml of iso-propanol

Sources & evidence

ORD record
ord-f4af990fa1ff49988392b2963adea897
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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