Dimethyl Sulfate → HCID 14859084, compound

HRID 484111Notes

Reaction equation

HRID 484111 reaction equation
[C:1]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([O:3][CH2:4][CH3:5])=[O:2].[C:21](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[C:1]([C:6]1[N:7]([CH3:21])[C:8]2[C:13]([C:14]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 11821846HCID 11821846, compound

Product 1

HCID 14859084HCID 14859084, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-Carboethoxy-3-indoleacetate (1 gm) in acetonitrile (50 ml) was combined with potassium carbonate (2 gm) and dimethyl sulfate (0.38 ml). The mixture was heated to reflux for 20 hours, filtered warm, and the solvent removed on the rotary evaporator. The residue was suspended in ether (150 ml) and the mixture washed with 5% hydrochloric acid (3×50 ml), 5% sodium bicarbonate (3×50 ml) and water (3×50 ml). The ether solution was dried over magnesium sulfate and the solvent removed on a rotary evaporator to provide the product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 20 hours
  3. filtrationfiltered
  4. temperaturewarm
  5. customthe solvent removed on the rotary evaporator
  6. washthe mixture washed with 5% hydrochloric acid (3×50 ml), 5% sodium bicarbonate (3×50 ml) and water (3×50 ml)
  7. dry with materialThe ether solution was dried over magnesium sulfate
  8. customthe solvent removed on a rotary evaporator
  9. customto provide the product

Sources & evidence

ORD record
ord-c9dde8605ecb4e55b1cf350495f70331
Source dataset
uspto-grants-1993_07
Patent number
US05229413

Reaction notes

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