Dimethyl Sulfate → HCID 11424750, compound

HRID 359212Notes

Reaction equation

HRID 359212 reaction equation
[CH:1]1[C:17]2[C:16]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:18]C(C)([O-])C.[K+].COS(OC)(=O)=O.[OH-].[Na+]>C(Cl)Cl.C1COCC1>[CH3:18][N:9]1[C:8]2[CH:7]=[CH:6][C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:17]=3[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 674597H-Benzo(c)carbazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 11424750HCID 11424750, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a RB flask equipped with magnetic stirring bar, reflux condenser and N2 inlet line with bubbler was added 7H-benzo[c]carbazole (H.G. Pars Pharmaceutical Laboratories, Inc., 6.6 g, 30.4 mmol) and dry THF (250 mL). To the flask was added in one portion potassium t-butoxide (Aldrich, 4.2 g, 37.4 mmol). Dimethylsulfate (Aldrich, 7.56 g, 60.0 mmol, 5.9 mL) was added dropwise to the solution and the mixture stirred for 15 min. TLC (SiO2 /PhCH3) showed the reaction to be complete. The reaction mixture was then poured into a 1N NaOH solution (2 L) and stirred. The white solid which formed was collected by filtration, washed with H2O (3×500 mL), sucked semidry, dissolved in PhCH3 (300 mL) and eluted through a plug of SiO2 (5×5 cm) using PhCH3 as the eluting solvent. Appropriate fractions were combined and the solvent removed to give a crude white product. This material was dissolved in CH2Cl2 (400 mL), filtered and diluted to 1 L with hexane. The mixture was concentrated to 500 mL by rotary evaporation. A white solid formed which was filtered, washed with pentane and dried in a vacuum to give 5.0 g of 7-methyl-7H-benzo[c]carbazole, mp 116°-118°, (C,H,N). A further 1.06 g of product was obtained on standing and further concentration of the filtrate to give a combined yield of 87.3%.

Workup

  1. customTo a RB flask equipped with magnetic stirring bar
  2. temperaturereflux condenser and N2 inlet line with bubbler
  3. customthe reaction
  4. stirringstirred
  5. customThe white solid which formed
  6. filtrationwas collected by filtration
  7. washwashed with H2O (3×500 mL)
  8. dissolutiondissolved in PhCH3 (300 mL)
  9. washeluted through a plug of SiO2 (5×5 cm)
  10. customthe solvent removed
  11. customto give a crude white product
  12. filtrationfiltered
  13. additiondiluted to 1 L with hexane
  14. concentrationThe mixture was concentrated to 500 mL by rotary evaporation
  15. customA white solid formed which
  16. filtrationwas filtered
  17. washwashed with pentane
  18. customdried in a vacuum

Sources & evidence

ORD record
ord-7e40b42360dc46cead55ab991d91b6a7
Source dataset
uspto-grants-1991_03
Patent number
US04999369

Reaction notes

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