Methyl iodide → HCID 11770078, compound

HRID 1267173Notes

Reaction equation

HRID 1267173 reaction equation
[H-].[Na+].[CH:3]1[C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH2:10][C:9](=[O:18])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:19]I>CN(C=O)C.C(Cl)Cl.O>[CH3:19][CH:10]1[C:9](=[O:18])[NH:8][C:7]2[CH:6]=[CH:5][CH:4]=[CH:3][C:13]=2[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]1=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 113677988-Azatricyclo[9.4.0.0,2,7]pentadeca-1(15),2,4,6,11,13-hexaen-9-one

Product 1

HCID 11770078HCID 11770078, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
60 °C

Procedure

A round bottom flask was charged with sodium hydride (0.295 g, 7.46 mmol) in 9.0 mL of DMF and treated with 5,7-dihydro-6H-dibenz[b,d]azepin-6-one (1.3 g, 6.22 mmol) (CAS #20011-90-9, prepared as described in Brown, et. al., Tetrahedron Letters, No. 8, 667-670, (1971) and references cited therein, which are incorporated herein by reference). After stirring at 60° C. for 1 hour, the solution was treated with methyl iodide (1.16 mL, 18.6 mmol) and stirring continued for 17 hours with the exclusion of light. After cooling, the reaction was diluted with CH2Cl2/H2O, washed with NaHSO4 solution, H2O, and dried over Na2SO4. Evaporation and flash chromatography (SiO2, CHCl3) gave 0.885 g (63%) of the title compound as a colorless solid.

Workup

  1. customprepared
  2. stirringstirring
  3. waitcontinued for 17 hours with the exclusion of light
  4. temperatureAfter cooling
  5. washwashed with NaHSO4 solution, H2O
  6. dry with materialdried over Na2SO4
  7. customEvaporation and flash chromatography (SiO2, CHCl3)

Sources & evidence

ORD record
ord-61a3ffde79de41b28e5e6f4941b9cb14
Source dataset
uspto-grants-2003_04
Patent number
US06552013B1

Reaction notes

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