Methyl iodide → HCID 9909216, compound

HRID 1939172Notes

Reaction equation

HRID 1939172 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[CH2:4][CH:3]1[NH:14][C:15](=[O:26])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25].[C:27](=O)([O-])[O-].[K+].[K+].IC.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:27][N:8]1[C:2](=[O:1])[CH:3]([NH:14][C:15](=[O:26])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH2:4][C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]1=2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 21467116HCID 21467116, compound

Product 1

HCID 9909216HCID 9909216, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100 mL round bottom flask was charged with N-(2,5-dioxo-3,4-dihydro-1H-benzo[b]azepin-3-yl)-3-(2,4-dichlorophenyl)-propionamide (2.5 g, 6.38 mmole), potassium carbonate (1.76 g, 12.7 mmole), DMF (20 mL), and iodomethane (3.55 g, 25 mmole). The reaction mixture was stirred at room temperature for 5 hr. and then poured into saturated sodium bicarbonate (500 mL). The aqueous mixture was extracted with ethyl acetate (3×200 mL). The combined organics were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The resulting solid was swished with a minimum of warm ether and filtered to give 2.1 g (81%) of the product. mp 182°-184° C.

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate (3×200 mL)
  2. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0675aee7d5b24d2c90f291fe382ccb99
Source dataset
uspto-grants-1997_12
Patent number
US05696111

Reaction notes

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