Methyl iodide → HCID 86741346, compound

HRID 1906146Notes

Reaction equation

HRID 1906146 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=2[NH:6][CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH3:27]I>CN(C)C=O.C(OCC)(=O)C>[CH3:27][N:6]1[C:5]2[CH:23]=[CH:24][CH:25]=[CH:26][C:4]=2[NH:3][C:2]([CH3:1])=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 13763174HCID 13763174, compound

Product 1

HCID 86741346HCID 86741346, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture containing 2,5-dihydro-4-methyl-2-(3-nitrophenyl)-1H-1,5-benzodiazepine-3-carboxylic acid, ethyl ester (1,5 g., 4.25 mmole) in dry dimethylformamide (5 ml.) is treated with methyl iodide (581 mg., 5.5 mmole) and then allowed to stir at room temperature for 24 hours. The reaction mixture is diluted with ethyl acetate and is washed with sodium bicarbonate, water, and brine. After drying over magnesium sulfate, the solvent is evaporated and the residue is purified by flash chromatography on silica gel (30% ethyl acetate in hexanes). The yellow foam obtained (701 mg.) is crystallized from ether-hexanes to provide yellow crystalline 2,5-dihydro-1,4-dimethyl-2-(3-nitrophenyl)-1H-1,5-benzodiazepine-3-carboxylic acid, ethyl ester; m.p. 113°-115.5°. TLC (silica gel; ethyl acetate:hexanes, 1:1) Rf =0.5.

Workup

  1. washis washed with sodium bicarbonate, water, and brine
  2. dry with materialAfter drying over magnesium sulfate
  3. customthe solvent is evaporated
  4. customthe residue is purified by flash chromatography on silica gel (30% ethyl acetate in hexanes)
  5. customThe yellow foam obtained (701 mg.)
  6. customis crystallized from ether-hexanes

Sources & evidence

ORD record
ord-76e4db87f30c43a1b35adb89be7bc63d
Source dataset
uspto-grants-1987_03
Patent number
US04650797

Reaction notes

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