Indole → HCID 44596163, compound

HRID 1675321Notes

Reaction equation

HRID 1675321 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(CC)CC)C.[N+:17]([C:20]1[CH:21]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18].ClCCl>ClCCCl>[N+:17]([C:20]1[CH:21]=[C:22]([S:26]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 798IndoleHCID 6344DichloromethaneHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 44596163HCID 44596163, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

Indole (17.09 mmol, 2.0 grams) was taken in 1,2-dichloroethane (20 mL) in 100 mL three necked round-bottomed flask. Triethylamine (34.19 mmol, 3.45 grams) was added to it at 25° C. The above mixture was added to solution of 3-nitrobenzenesulfonyl chloride (25.64 mmol, 5.68 grams) (obtained from step (i)) and dichloromethane (25 mL), while maintaining the temperature below 10° C. The reaction mixture was then stirred for a period of 24 hours at 25° C. After the completion of reaction, the reaction mixture was poured onto ice-water mixture under stirring and the product was extracted with ethyl acetate (2×30 mL). The combined ethyl acetate extracts were then washed with water, brine and dried over anhydrous magnesium sulfate. The volatiles were removed under the reduced pressure to obtain 5.4 grams of thick syrupy mass, which was purified by column chromatography using silicagel (100-200 mesh), eluent being ethyl acetate and n-hexane (5:95),

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. customAfter the completion of reaction
  3. additionthe reaction mixture was poured onto ice-water mixture
  4. stirringunder stirring
  5. extractionthe product was extracted with ethyl acetate (2×30 mL)
  6. washThe combined ethyl acetate extracts were then washed with water, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe volatiles were removed under the reduced pressure
  9. customto obtain 5.4 grams of thick syrupy mass, which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-532a8eeb38764c77a7e6318d3cbf17b9
Source dataset
uspto-grants-2011_08
Patent number
US08003670B2

Reaction notes

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