Triethylamine → HCID 22611238, compound

HRID 1463315Notes

Reaction equation

HRID 1463315 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.[CH2:18]([S:20](Cl)(=[O:22])=[O:21])[CH3:19]>C(Cl)Cl>[CH2:18]([S:20]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)(=[O:22])=[O:21])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 788675-Aminoindole

Product 1

HCID 22611238HCID 22611238, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of 5-amino-1H-indole (10.0 g, 76 mmol) and triethylamine (15.8 mL, 114 mmol) in 100 mL CH2Cl2 at 0° C. was added dropwise a solution of ethanesulfonyl chloride (7.9 mL, 83 mmol) in 25 mL of CH2Cl2. The solution was allowed to slowly warm to 23° C. over 20 h. The reaction mixture was concentrated in vacuo and the residue dissolved in 400 mL of ethyl acetate. The organic layer was washed with 100 mL of water, 50 mL of 0.1M HCl, 50 mL of saturated NaHCO3 solution, and 50 mL of saturated NaCl solution. The organic layer was dried over anhydrous K2CO3, filtered, and concentrated in vacuo to obtain 5-ethanesulfonylamino-1H-indole (16.9 g, >99%) which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in 400 mL of ethyl acetate
  3. washThe organic layer was washed with 100 mL of water, 50 mL of 0.1M HCl, 50 mL of saturated NaHCO3 solution, and 50 mL of saturated NaCl solution
  4. dry with materialThe organic layer was dried over anhydrous K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1125879f57d847029f4967c15dae8e43
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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