Dimethyl Sulfate → HCID 6481889, compound

HRID 374024Notes

Reaction equation

HRID 374024 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][N:5]1[C:21](=[O:22])[C:20]2[C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:23][CH3:24])[CH:17]=4)[NH:12][C:11]=3[CH:10]=[CH:9][C:8]=2[C:6]1=[O:7].[H-].[Na+].S(OC)(O[CH3:32])(=O)=O>CN(C)C=O>[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][N:5]1[C:21](=[O:22])[C:20]2[C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:23][CH3:24])[CH:17]=4)[N:12]([CH3:32])[C:11]=3[CH:10]=[CH:9][C:8]=2[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 19808758HCID 19808758, compound

Product 1

HCID 6481889HCID 6481889, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

In 10 ml of N,N-dimethylformamide was dissolved 380 mg of N-(2-dimethylaminoethyl)-6-methoxycarbazole-3,4-dicarboximide. Thereto was added 45 mg of 60% sodium hydride. The mixture was stirred at 40° C. for 20 minutes and then cooled to 20° C. Thereto was added 140 mg of dimethyl sulfate, and the resulting mixture was stirred at the same temperature for 2 hours. The solvent was removed by distillation under reduced pressure. The residue was mixed with 50 ml of ethyl acetate and 25 ml of water to dissolve the residue. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from n-propanol to obtain 200 mg (yield: 50%) of N-(2-dimethylaminoethyl)-6-methoxy-9-methylcarbazole-3,4-dicarboximide as yellow crystals.

Workup

  1. temperaturecooled to 20° C
  2. stirringthe resulting mixture was stirred at the same temperature for 2 hours
  3. customThe solvent was removed by distillation under reduced pressure
  4. additionThe residue was mixed with 50 ml of ethyl acetate and 25 ml of water
  5. dissolutionto dissolve the residue
  6. customThe organic layer was separated
  7. washwashed with an aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue was recrystallized from n-propanol

Sources & evidence

ORD record
ord-c2e3c9c7a269429eb1529fb8b5111bc3
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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