Iodoethane → HCID 19750840, compound

HRID 484105Notes

Reaction equation

HRID 484105 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].[CH2:20](I)[CH3:21]>CN(C)C=O>[CH2:20]([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)[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10131121HCID 10131121, compound

Product 1

HCID 19750840HCID 19750840, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

To 25 ml of N,N-dimethylformamide is added 0.48 g of 60% sodium hydride followed by the dropwise addition of a solution of 1.976 g of 6-(methylsulfonyl)-benz[cd]indol-2(1H)-one (Example 3) in 50 ml of N,N-dimethylformamide. Stirring is continued for 20 minutes followed by heating at 50° C. for 10 minutes then cooling at room temperature. A solution of 1.872 g of ethyl iodide in 25 ml of N,N-dimethylformamide is added dropwise and stirring continued for 1.5 hours. The reaction mixture is poured over cracked ice and the solid collected, dried and crystallized from ethyl acetate to give 1.03 g of the desired product as a solid, m.p. 199°-203° C.

Workup

  1. temperaturethen cooling at room temperature
  2. stirringstirring
  3. waitcontinued for 1.5 hours
  4. additionThe reaction mixture is poured over cracked ice
  5. customthe solid collected
  6. customdried
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-63fc5693dd2d4b6697ccf3c5616ec072
Source dataset
uspto-grants-1993_07
Patent number
US05229411

Reaction notes

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