Dimethylformamide → HCID 10490904, compound

HRID 1081531Notes

Reaction equation

HRID 1081531 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[Cu][C:17]#[N:18].[C-]#N.[K+].CN(C)[CH:24]=[O:25]>O>[C:17]([C:6]1[C:7]([O:25][CH3:24])=[CH:8][C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:3]([CH2:1][CH3:2])[C:4]=2[CH:5]=1)#[N:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6836N-ethyl carbazoleHCID 9032Potassium CyanideHCID 178418546HCID 178418546, compound

Product 1

HCID 10490904HCID 10490904, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 9-ethylcarbazole (13.0 g, 0.0428 mole) and copper(I) cyanide (4.60 g, 0.0513 mole) in 15 ml of N,N-dimethylformamide were boiled under reflux for 19 hours with powerful magnetic stirring. All dissolved within 40 min. When cooled to ≈60° the mixture was treated with a solution of 10.5 g of potassium cyanide in 35 ml of water, and stirred 1 hour. The solid was filtered, the lumps being broken up, washed on the Buchner with 250 ml of water, and dried to give 11.0 g of crude 2-cyano-9-ethyl-3-methoxy carbazole, m.p. 145°-155°. This was extracted from a Soxhlet overnight with 250 ml of heptane and the extract was cooled in ice to give 9.70 g (91%), m.p. 148°-155.5°. TLC on MK6F Silca Gel, t-butyl methyl ether, UV showed 5-10% of a non-fluorescent impurity at Rf=0.65 and 90-95% ArCN with a blue fluorescence at Rf=0.69. This was used in the next reaction.

Workup

  1. temperatureunder reflux for 19 hours with powerful magnetic stirring
  2. dissolutionAll dissolved within 40 min
  3. temperatureWhen cooled to ≈60° the mixture
  4. filtrationThe solid was filtered
  5. washwashed on the Buchner with 250 ml of water
  6. customdried

Sources & evidence

ORD record
ord-7fb401e741ef4932999144d4da7555e8
Source dataset
uspto-grants-1996_12
Patent number
US05587112

Reaction notes

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