Pyridine → HCID 22625143, compound

HRID 279431Notes

Reaction equation

HRID 279431 reaction equation
O[CH:2]([CH2:18][CH2:19][CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1.CCCCCC.CC[O:45]CC>>[C:21]1([S:27]([O:29][CH:3]([CH2:2][CH2:18][CH2:19][CH3:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])(=[O:45])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 21584099Diethylether hexaneHCID 22625144HCID 22625144, compound

Product 1

HCID 22625143HCID 22625143, compoundYield 83%

Procedure

Compound 7 (0.83 g, 2.7 mmol) was caused to react with benzenesulfonylchloride (0.45 ml, 3.5 mmol) and pyridine (3.5 mmol) in CHCl2 (20 mL) at 5° C. for 20 hr. The mixture was ice-diluted HCl, and the organic layer separated, dried (MgSO4 and evaporated under reduced pressure. The product 8 (1.0 g. 83% yield) was isolated as an oil by column chromatography (hexane/ether 1:1). TLC (hexane/ether 1:1) Rf=0.5. 1H-NMR δ0.82 (t, 3H, C(16)H2), 1.4 (m, 18H, CH2), 2.52 (t, 2H, C(2)H2), 2.62 (t, 2H, C(5)H2), 2.78 (t, 2H, C(3)H23.70 (s, 3H, —COO—CH3), 4.60 (m, 1H, C(13)H), 7.7 (m, 5H, aryl).

Workup

  1. customthe organic layer separated
  2. dry with materialdried (MgSO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d9a920b25832415ea8c78427c0630267
Source dataset
uspto-grants-2002_03
Patent number
US06362352B1

Reaction notes

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