Water → HCID 12798072, compound

HRID 1659526Notes

Reaction equation

HRID 1659526 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[C:17]2[CH:16]3[CH2:18][CH2:19][CH:13]([CH2:14][CH:15]3[NH:20][CH:21]=[O:22])[C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:4].O.[CH3:24]I>C1(C)C(C)=CC=CC=1>[CH2:3]([N:5]1[C:17]2[CH:16]3[CH2:18][CH2:19][CH:13]([CH2:14][CH:15]3[N:20]([CH3:24])[CH:21]=[O:22])[C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 20559330HCID 20559330, compound

Product 1

HCID 12798072HCID 12798072, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

To a stirred suspension of sodium hydride (0.5 g of 57% oil dispersion, 0.011 mole) in dry xylene (15 ml), a solution of N-(9-ethyl-2,3,4,9-tetrahydro-1,4-ethano-1H-carbazol-2-yl)-formamide (0.9 g, 0.0034 mole, described in Example 6) in dry xylene (15 ml) was added dropwise under nitrogen. The suspension was refluxed with stirring for 18 hr. The reaction mixture was cooled. The water condenser was replaced by a dry ice/acetone condenser and methyl iodide (1.7 ml) was added. The reaction mixture was refluxed for 5 hr. Additional 1.7 ml of methyl iodide was added. The solution was refluxed for 4 hr and stirred at 20° C. for 18 hr. The reaction mixture was cooled in ice, and water was added dropwise to destroy the excess hydride. The compound was extracted with ethyl acetate and the organic layer was washed with water, dried and evaporated to afford the title compound as a yellow oil (ca. 1.2 g): IR (CHCl3) 1650 cm-1.

Workup

  1. temperatureThe suspension was refluxed
  2. temperatureThe reaction mixture was cooled
  3. temperatureThe reaction mixture was refluxed for 5 hr
  4. temperatureThe solution was refluxed for 4 hr
  5. stirringstirred at 20° C. for 18 hr
  6. temperatureThe reaction mixture was cooled in ice
  7. customto destroy the excess hydride
  8. extractionThe compound was extracted with ethyl acetate
  9. washthe organic layer was washed with water
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-62182918733d43e08cf3fa1ef653b9e1
Source dataset
uspto-grants-1981_12
Patent number
US04304772

Reaction notes

Loading…