Methyl iodide → HCID 19427677, compound

HRID 1078545Notes

Reaction equation

HRID 1078545 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[NH:6][C:7](=[S:19])[C:8]3[CH:18]=[CH:17][CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[N:6]=[C:7]([S:19][CH3:23])[C:8]3[CH:18]=[CH:17][CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19427669HCID 19427669, compound

Product 1

HCID 19427677HCID 19427677, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5,11-dihydro-2,4-dimethyl-11-ethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-thione (0.2 g, 0.7 mmol) in dimethylformamide (10 mL) was added NaH (50% in mineral oil, 0.04 g, 0.8 mmol). The mixture was stirred under argon at 40° C. for 1 hr. After cooling to 30° C. methyl iodide (0.12 g, 0.8 mmol) was added, and the mix was stirred for 1 hr. The reaction was quenched with water, and the mixture was concentrated in vacuo. The residue was treated with ethyl acetate, washed, dried, and concentrated. Chromatography over silica gel (eluted with 20% EtOAc/Hex) gave 0.2 g of the title compound, m.p. 130°-132° C.

Workup

  1. additionwas added
  2. stirringthe mix was stirred for 1 hr
  3. customThe reaction was quenched with water
  4. concentrationthe mixture was concentrated in vacuo
  5. additionThe residue was treated with ethyl acetate
  6. washwashed
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c557e4fa8cc249f88e74f499d13c7537
Source dataset
uspto-grants-1996_08
Patent number
US05550117

Reaction notes

Loading…