Water → HCID 22675433, compound

HRID 1005969Notes

Reaction equation

HRID 1005969 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][S:13][C:14]1[NH:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.[C:23](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[CH3:23][N:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]=[C:14]1[S:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 9796852HCID 9796852, compound

Product 1

HCID 22675433HCID 22675433, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.2 g of (Compound 1) was dissolved in 1.2 ml of DMF, added with 0.27 g of potassium carbonate and 0.12 g of methyl iodide and the mixture was stirred at 50° C. for 1.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:6) to obtain 0.15 g of the title compound (yield: 72%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:6)

Sources & evidence

ORD record
ord-665c126270824b81b398ea884a80c6ce
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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