Methyl iodide → HCID 57273375, compound

HRID 361320Notes

Reaction equation

HRID 361320 reaction equation
[OH:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]([NH2:16])=[O:15])[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[CH2:4]1.[OH-].[K+].I[CH3:24]>CC(C)=O.O>[CH3:24][O:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]([NH2:16])=[O:15])[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[CH2:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 85040065Bia-2-024

Product 1

HCID 57273375HCID 57273375, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 0.2 g (0.75 mmol) of 10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide in 2 mL of acetone cooled to 0° C. was added a solution of 0.065 g (1.16 mmol) of potassium hydroxide in 1 mL of water followed by 0.164 g (1.16 mmol) of iodomethane. The resulting mixture was stirred at room temperature overnight then 10 mL of water was added. The mixture was extracted with ether and the organic layer was washed with water and brine, then dried by sodium sulphate and filtered. The solvent was removed by evaporation under reduced pressure and the residue chromatographed on silica gel with a 3% methanol-dichloromethane mixture. Chromatographically homogenous fractions were pooled, the solvents were removed under reduced pressure and the residue was crystallised from toluene to give the product as off-white crystals of m.p. 157.9°-159.4° C.

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried by sodium sulphate
  4. filtrationfiltered
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customthe residue chromatographed on silica gel with a 3% methanol-dichloromethane mixture
  7. customthe solvents were removed under reduced pressure
  8. customthe residue was crystallised from toluene

Sources & evidence

ORD record
ord-88242fb3bb8b4ba8bc0e723b0f22bb5f
Source dataset
uspto-grants-1999_02
Patent number
US05866566

Reaction notes

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