Methyl iodide → HCID 19750820, compound

HRID 484100Notes

Reaction equation

HRID 484100 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[C:8]2[C:9]3[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[C:10]=3[CH:17]=[CH:18][CH:19]=2)(=[O:6])=[O:5].[CH3:20]I>CN(C)C=O>[CH3:20][N:12]1[C:13]2[C:9]3[C:8](=[CH:19][CH:18]=[CH:17][C:10]=3[C:11]1=[O:16])[C:7]([S:4]([CH3:3])(=[O:6])=[O:5])=[CH:15][CH:14]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10131121HCID 10131121, compound

Product 1

HCID 19750820HCID 19750820, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

To 25 ml of N,N-dimethylformamide is added 0.6 g of 60% sodium hydride under argon, followed by the rapid dropwise addition of a solution of 2.5 g of 6-(methylsulfonyl)-benz[cd]indol-2(1H)-one (Example 3) dissolved in 50 ml of N,N-dimethylformamide. The mixture is stirred for 20 minutes then heated at 50° C. for minutes followed by cooling to room temperature. While stirring, a solution of 2.14 g of methyl iodide in 25 ml of N,N-dimethylformamide is added dropwise. The stirring is continued at room temperature for 2 hours. The reaction mixture is poured over 200 ml of crushed ice and the resulting solid collected, washed with water and dried to afford 2.54 g of the desired product, m.p. 216°-218° C.

Workup

  1. temperatureby cooling to room temperature
  2. stirringWhile stirring
  3. waitThe stirring is continued at room temperature for 2 hours
  4. customthe resulting solid collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b7edcc63b5d949328b98e84d8a77985a
Source dataset
uspto-grants-1993_07
Patent number
US05229411

Reaction notes

Loading…