Methyl iodide → HCID 11770078, compound

HRID 987663Notes

Reaction equation

HRID 987663 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). After stirring at 60° C. for 1 h, the solution was treated with methyl iodide (1.16 ml, 18.6 mmol) and stirring continued for 17 h 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 h 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-9ca7c004cdec410c8c3da0630ffaf27b
Source dataset
uspto-grants-2003_10
Patent number
US06632811B2

Reaction notes

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