Methyl iodide → 3,6-dibromo-9-methyl-1-nitro-9h-carbazole

HRID 359666Notes

Reaction equation

HRID 359666 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[CH3:19]I.[H-].[Na+]>CS(C)=O.CCCCC>[Br:1][C:2]1[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]2[N:6]([CH3:19])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2217653,6-Dibromo-1-nitro-9H-carbazole

Product 1

HCID 2587513,6-dibromo-9-methyl-1-nitro-9h-carbazole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8003PentaneSolvent

Procedure

3,6-dibromo-1-nitrocarbazole (3.56 g, 0.01 mole) was dissolved in 30 ml of warm DMSO followed by the addition of 30 ml of CH3I. Then 2.0 g of 50% NaH dispersion in mineral oil (0.02 mole) was washed under N2 with 2×50 ml of pentane, dried under N2 and added rapidly to the DMSO solution. The solution turned purple immediately with H2 evolution and became yellow in two minutes. Addition of 0.25 g of NaH did not cause the yellow slurrY to turn purple indicating that the reaction was complete. Methanol (200 ml) was added cautiously to precipitate the product. The product was recovered by filtration, washed with 25 ml of methanol, 10×25 ml of water, 25 ml of methanol and air dried to give 3.40 g of product, m.p. 225°-226° C. (corrected). [H. Lindemann & F. Muhlhaus, Ber., 58, 2371 (1925) report a m.p. of 221° C. for the product].

Workup

  1. customdried under N2
  2. additionadded rapidly to the DMSO solution
  3. additionAddition of 0.25 g of NaH
  4. additionMethanol (200 ml) was added cautiously
  5. customto precipitate the product
  6. filtrationThe product was recovered by filtration
  7. washwashed with 25 ml of methanol, 10×25 ml of water, 25 ml of methanol and air
  8. customdried

Sources & evidence

ORD record
ord-8bb18ae3fa0c462d96f89e48e0b033fe
Source dataset
uspto-grants-1991_03
Patent number
US05002856

Reaction notes

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