Methyl iodide → HCID 19608163, compound

HRID 1603124Notes

Reaction equation

HRID 1603124 reaction equation
CN(C)[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1.CI>C(Cl)(Cl)Cl>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:3]=[CH:4][CH2:5][CH2:6]2)=[O:31])=[CH:20][CH:19]=1)=[O:30]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 10837161HCID 10837161, compound

Product 1

HCID 19608163HCID 19608163, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-dimethylamino-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (10 g), methyl iodide (1.7 ml) and chloroform (10 ml) is heated with stirring at 100° C. for 3 hours in an autoclave. After completion of the reaction, the solvent is distilled off under reduced pressure and the resulting residue is dissolved in methanol. The mixture is treated with IRA-400 (trade mark; Organo Co., Ltd., OH- type). Methanol is distilled off and the resulting residue is suspended in t-butyl alcohol (90 ml), and thereto is added potassium t-butoxide (2.3 g). The mixture is refluxed for 5 hours. The solvent is distilled off under reduced pressure, and the resulting residue is dissolved in dichloromethane. The mixture is washed successively with water and saturated saline solution and dried over magnesium sulfate. The solvent is distilled off and to the resulting residue is added dichloromethane/diethyl ether. The precipitated crude crystal is recrystallized from ethanol to give 1-[4-(2-chlorobenzoylamino)benzoyl]-2,3-dihydro-1H-benzazepine (5.15 g) as colorless needles, m.p. 205-207° C.

Workup

  1. temperatureis heated
  2. customAfter completion of the reaction
  3. distillationthe solvent is distilled off under reduced pressure
  4. dissolutionthe resulting residue is dissolved in methanol
  5. additionThe mixture is treated with IRA-400 (trade mark; Organo Co., Ltd., OH- type)
  6. distillationMethanol is distilled off
  7. additionis added potassium t-butoxide (2.3 g)
  8. temperatureThe mixture is refluxed for 5 hours
  9. distillationThe solvent is distilled off under reduced pressure
  10. dissolutionthe resulting residue is dissolved in dichloromethane
  11. washThe mixture is washed successively with water and saturated saline solution
  12. dry with materialdried over magnesium sulfate
  13. distillationThe solvent is distilled off and to the resulting residue
  14. additionis added dichloromethane/diethyl ether
  15. customThe precipitated crude crystal
  16. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-f3c7d126776d4d73b23c008f6430bfe5
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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