Methyl iodide → HCID 13067128, compound

HRID 223497Notes

Reaction equation

HRID 223497 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[C:7](=[CH:20][NH:21][CH:22]=3)[CH:8]([O:18][CH3:19])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[CH3:25]C(C)([O-])C.[K+].CI>CN(C)C=O.O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[C:7](=[CH:20][N:21]([CH3:25])[CH:22]=3)[CH:8]([O:18][CH3:19])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 136165693HCID 136165693, compound

Product 1

HCID 13067128HCID 13067128, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In one portion 1.0 g (2.8 mmol) of 8-chloro-6-(2-chlorophenyl)-4-methoxy-2H,4H-pyrrolo[3,4-d][2]benzazepine was added to a solution of 0.35 g (3.0 mmol) of potassium t-butoxide in 20 ml of dimethylformamide which was cooled to 0°. After stirring for 15 min, 0.3 ml (4.8 mmol) of methyl iodide was added. The mixture was stirred for 5 min, diluted with water and extracted with ether. The ether solution was washed with water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to give a pale yellow oil. Purification by column chromatography (silica gel, 25 g; 5% ether in methylene chloride, eluent) gave an off-white solid, mp 128°-130°. Recrystallization from a mixture of ether and petroleum ether gave off-white prisms, mp 128°-130°.

Workup

  1. temperaturewas cooled to 0°
  2. stirringThe mixture was stirred for 5 min
  3. extractionextracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customto give a pale yellow oil
  8. customPurification by column chromatography (silica gel, 25 g; 5% ether in methylene chloride, eluent)
  9. customgave an off-white solid, mp 128°-130°
  10. customRecrystallization
  11. additionfrom a mixture of ether and petroleum ether
  12. customgave off-white prisms, mp 128°-130°

Sources & evidence

ORD record
ord-8ec66601af024b4580a2a214afdd845f
Source dataset
uspto-grants-1982_10
Patent number
US04354973

Reaction notes

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