Methyl iodide → HCID 474639, compound

HRID 1415667Notes

Reaction equation

HRID 1415667 reaction equation
[CH3:1][S:2][CH:3]1[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[N:6]([CH3:15])[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[N:19][C:4]1=2.[CH3:22]C(C)([O-])C.[K+].CI>CS(C)=O.C(OCC)(=O)C>[CH3:22][C:3]1([S:2][CH3:1])[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[N:6]([CH3:15])[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[N:19][C:4]1=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 474638HCID 474638, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 474639HCID 474639, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5,11-dihydro-11-methylthio-2-methoxy-5-methyl-dipyrido[3,2-b:2',3'-e]azepine-6-one (0.031 g) in DMSO (0.5 mL) stirred under argon was added potassium tert-butoxide (1M in tetrahydrofuran, 0.012 mL). After 1 minute, methyl iodide (0.05 mL) was added. After 5 minutes the mixture was diluted with ethyl acetate, washed with water, dried, filtered and evaporated. Fractionation of the residue by preparative layer chromatography (developer, ethyl acetate/hexane) gave 5,11-dihydro-11-methyl-11-methylthio-2-methoxy-5-methyl-dipyrido[3,2-b:2',3'-e]azepine-6-one (0.029).

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-3dda6a5781c84537b9f67e00ef439322
Source dataset
uspto-grants-1999_06
Patent number
US05908841

Reaction notes

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