Hydrochloric Acid → HCID 11709429, compound

HRID 966058Notes

Reaction equation

HRID 966058 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>N1C=CC=CC=1>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 22314380HCID 22314380, compound

Product 1

HCID 11709429HCID 11709429, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-acetyl-5-aminoindole (1.57 g, 9 mmol) in pyridine is treated dropwise at 0° C. with benzenesulfonyl chloride (1.25 g, 9.9 mmol), stirred for 16 h at ambient temperatures, poured into dilute aqueous HCl and extracted with ethyl acetate. The combined extracts are washed sequentially with water and brine, dried over Na2SO4 and concentrated in vacuo to afford the title product as a white solid, 2.8 g (99% yield), identified by NMR and mass spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts are washed sequentially with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d06934d12dc04a129fa030a7104b73fd
Source dataset
uspto-grants-2005_10
Patent number
US06951881B2

Reaction notes

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