Methyl iodide → HCID 21467113, compound

HRID 1939174Notes

Reaction equation

HRID 1939174 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[C:11](=[O:21])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:22][N:14]1[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[C:11](=[O:21])[CH2:10][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:15]1=[O:16]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 146664143-t-butyloxycarbonylamino-3,4-dihydro-1H-1-benzazepine-2,5-dione

Product 1

HCID 21467113HCID 21467113, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-tertbutyloxycarbonylamino-2,3,4,5-tetrahydro-2,5-dioxobenzo[b]azepine (5 g, 17.2 mmole) in DMF (50 mL) was treated with potassium carbonate (4.76 g, 34.4 mmole) and methyl iodide (4.88 g, 34.4 mmole). The reaction was stirred at ambient temperature for 4 hours. The mixture was diluted with ethyl acetate (300 ml) and saturated aqueous sodium hydrogen carbonate (500 ml). The organic layer was separated and the aqueous layer was extracted again with ethyl acetate (2×300 ml). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting solid was swished with warm ethyl ether (200 mL) and collected by filtration to give 4.1 g of the product. mp 205°-206° C.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted again with ethyl acetate (2×300 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2fba4eab9f0549438b2d76d3fe60ee69
Source dataset
uspto-grants-1997_12
Patent number
US05696111

Reaction notes

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