Lithium iodide → HCID 11583412, compound

HRID 2239656Notes

Reaction equation

HRID 2239656 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=2)=[C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:6]1(=[O:33])=[O:32])([CH3:4])([CH3:3])[CH3:2].[Li+].[I-]>N1C=CC=CC=1>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:6]1(=[O:32])=[O:33])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 67243496HCID 67243496, compound

Product 1

HCID 11583412HCID 11583412, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 4-{3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propoxy}benzoate (0.90 g, 0.19 mmol) and LiI (0.382 g, 2.86 mmol) was dissolved in dry pyridine (1 mL) and heated at reflux for 4 h and then left at rt over night. The reaction mixture was purified by flash chromatography using first Hexane and EtOAc and then EtOAc and MeOH as eluant giving the title compound (0.003 g, 3.4%). 1H NMR (CD3CN): 7.98 (d, 2H), 7.56-7.48 (m, 5H), 6.90 (d, 2H), 6.02 (t, 1H), 3.90 (t, 2H), 3.12-3.08 (m, 2), 1.82-1.76 (t, 2H), 1.17 (s, 9H); Mass Spectrum: M+H+ 459.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. waitleft at rt over night
  4. customThe reaction mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-dd35d1717da341aba4fe64db466149c5
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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