Ethanol → HCID 19427671, compound

HRID 1078542Notes

Reaction equation

HRID 1078542 reaction equation
[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[S:15])[NH:7][C:6]3[C:16]([CH3:20])=[CH:17][CH:18]=[N:19][C:5]2=3)[CH2:3][CH2:2]1.[H-].[Na+].IC.[CH2:25](O)C>CN(C)C=O>[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8]([S:15][CH3:25])=[N:7][C:6]3[C:16]([CH3:20])=[CH:17][CH:18]=[N:19][C:5]2=3)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15221258HCID 15221258, compound

Product 1

HCID 19427671HCID 19427671, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a warm (40° C.) solution of 1.0 g (3.54 mmol) of 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-thione in 25 mL of dry dimethylformamide under argon was added 200 mg (4.43 mmol) of a 60% sodium hydride on mineral oil dispersion. The suspension was heated at 60° for 30 min., cooled to 40° C., and 0.3 mL (4.43 mmol) of iodomethane was added in one portion. After stirring the mixture for 1 hr at room temperature, ethanol was added dropwise until bubbling ceased. The mixture was then poured over 200 mL of water, and the product was extracted with 2×200 mL of ethyl ether. The combined organics were washed with 300 mL of water, dried (Na2SO4), and concentrated. The resulting reddish solid was flash chromatographed over silica gel (eluted with 83% methylene chloride/ethyl acetate) to give a yellow solid. Recrystallization from ethyl ether/petroleum ether gave 350 mg of the title compound, m.p. 173°-177° C.

Workup

  1. temperatureThe suspension was heated at 60° for 30 min.
  2. customuntil bubbling
  3. additionThe mixture was then poured over 200 mL of water
  4. extractionthe product was extracted with 2×200 mL of ethyl ether
  5. washThe combined organics were washed with 300 mL of water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customchromatographed over silica gel (eluted with 83% methylene chloride/ethyl acetate)
  9. customto give a yellow solid
  10. customRecrystallization from ethyl ether/petroleum ether

Sources & evidence

ORD record
ord-2ccc9b18ef4948118cafa7d6e1a3ea07
Source dataset
uspto-grants-1996_08
Patent number
US05550117

Reaction notes

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