Tetrahydrofuran → HCID 25103524, compound

HRID 1675325Notes

Reaction equation

HRID 1675325 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.O1CCCC1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35]Cl>[OH-].[Na+].O>[CH3:32][N:33]([CH2:34][CH2:35][O:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1)[CH3:37]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 59272903HCID 59272903, compound

Product 1

HCID 25103524HCID 25103524, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

1-(3′-Hydroxybenzenesulfonyl) indole (0.602 mmol, 0.163 grams) (obtained from preparation 1) was taken in 50 mL two neck round bottom flask and added tetrahydrofuran (7 mL). To the above mixture potassium carbonate (1.24 mmol, 0.171 grams) was added and stirred for a period of 15-20 minutes. The free base generated from 2-dimethylaminoethyl chloride hydrochloride (2.48 mmol, 0.358 grams), by dissolving it in a solution of 3 mL 40% aqueous sodium hydroxide, diluted with 5 mL water and extracting free base with toluene (3 mL) was directly charged to reaction mixture. Reaction mixture was kept on reflux temperature and the progress was monitored. After completion of reaction, the reaction mass was cooled to room temperature, poured onto 25 mL of water and extracted the product with ethyl acetate (10 mL×4). Combined organic extracts were dried over sodium sulfate and the volatiles were removed under the reduced pressure to obtain 0.214 grams crude compound. The compound was purified by column chromatography using silica gel (100-200 mesh), the eluents being ethyl acetate and n-hexane (2:3) to obtain pure compound.

Workup

  1. extractionextracting free base with toluene (3 mL)
  2. additionwas directly charged to reaction mixture
  3. customReaction mixture
  4. temperatureon reflux temperature
  5. customAfter completion of reaction
  6. extractionextracted the product with ethyl acetate (10 mL×4)
  7. dry with materialCombined organic extracts were dried over sodium sulfate
  8. customthe volatiles were removed under the reduced pressure

Sources & evidence

ORD record
ord-5a6be442a367484ab715ea8588cdd398
Source dataset
uspto-grants-2011_08
Patent number
US08003670B2

Reaction notes

Loading…