Ethylene Glycol → HCID 21543497, compound

HRID 1606505Notes

Reaction equation

HRID 1606505 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][C:27](=O)[CH3:28].O>C1C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH:27]([CH:28]1[O:4][CH2:1][CH2:2][O:3]1)[CH3:5]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 21543500HCID 21543500, compound

Product 1

HCID 21543497HCID 21543497, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

38g (0.61 mole) of ethylene glycol and 1.4 g of paratoluene sulphonic acid are added to 6.35g of 5-chloro-3-(2-oxopropyl)indole dissolved in 320 ml of anhydrous benzene. This mixture is brought to reflux and held thereat for 3 hours, the water formed being separated. The reaction mixture is dissolved in an aqueous solution of sodium bicarbonate and filtered to eliminate the insoluble material. The organic phase is decanted, dried and concentrated. The product obtained is recrystallised from ethanol.

Workup

  1. temperatureto reflux
  2. custombeing separated
  3. dissolutionThe reaction mixture is dissolved in an aqueous solution of sodium bicarbonate
  4. filtrationfiltered
  5. customThe organic phase is decanted
  6. customdried
  7. concentrationconcentrated
  8. customThe product obtained
  9. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-3eea40b6f35a4372843cb2b4077b7713
Source dataset
uspto-grants-1976_04
Patent number
US03953442

Reaction notes

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