Dimethyl Sulfoxide → N-(1,3,4,9-tetrahydro-9-methyl-2H-carbazol-2-yl)acetamide

HRID 126897Notes

Reaction equation

HRID 126897 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH:2]1[NH:14][C:15](=[O:17])[CH3:16].[OH-].[K+].[CH3:20]S(C)=O.CI>O>[CH3:20][N:12]1[C:13]2[CH2:1][CH:2]([NH:14][C:15](=[O:17])[CH3:16])[CH2:3][CH2:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 20529236N-(1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

Product 1

HCID 20529228N-(1,3,4,9-tetrahydro-9-methyl-2H-carbazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.1 mol of N-(1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide, 0.15 mol of powdered KOH, and 75 ml of DMSO was stirred under nitrogen for 2 hr at room temperature. Methyl iodide (0.15 mol) was added in one portion, and, after brief cooling to moderate the exothermic reaction, the mixture was stirred at room temperature for 2 hr. The precipitate obtained by pouring the reaction mixture into excess water, was filtered, washed with water, and recrystallized from ethyl acetate to give the title compound, mp 171°-172°.

Workup

  1. temperatureafter brief cooling
  2. customthe exothermic reaction
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. customThe precipitate obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bedbbe95b0124840a548fac5176ad48b
Source dataset
uspto-grants-1981_03
Patent number
US04254134

Reaction notes

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