Pyridine → HCID 821545, compound

HRID 2378038Notes

Reaction equation

HRID 2378038 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.N1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1([S:27](Cl)(=[O:29])=[O:28])C2C(=CC=CC=2)C=CC=1.C(O[CH2:35][CH3:36])(=O)C.[CH2:37]1[CH2:41]OC[CH2:38]1>>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:27]([C:12]2[CH:36]=[CH:35][C:41]3[C:14](=[CH:15][CH:16]=[CH:38][CH:37]=3)[CH:13]=2)(=[O:29])=[O:28])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 5

HCID 1049PyridineHCID 7468p-AminoacetophenoneHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 665601-Naphthalenesulfonyl chloride

Product 1

HCID 821545HCID 821545, compound

Procedure

4′-Amino acetophenone (1.20 g, 5.29 mmol) was dissolved in THF (8 ml) before pyridine (1.28 ml, 15.8 mmol) was added, leaving a yellow solution. The naphthalenesulfonylchloride (0.715 g, 5.29 mmol) was then added dropwise with stirring. After stirring for 5 hours, THF and pyridine were removed in vacuo. The desired sulfonamide (1.074 g, 3.30 mmol, 62%) was recrystallized from ethyl acetate and hexanes. It had LC-MS (ES+): 326 [MH]+ m/e

Workup

  1. additionwas added
  2. customleaving a yellow solution
  3. stirringAfter stirring for 5 hours
  4. customTHF and pyridine were removed in vacuo

Sources & evidence

ORD record
ord-ef47185f88d9435ab2921359071170ab
Source dataset
uspto-grants-2008_12
Patent number
US07470722B2

Reaction notes

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