Lithium iodide → HCID 9820917, compound

HRID 1596533Notes

Reaction equation

HRID 1596533 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=[C:13]2[C:21]([O:23]CC)=[O:22])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[I-].[Li+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=[C:13]2[C:21]([OH:23])=[O:22])(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 21702184HCID 21702184, compound

Product 1

HCID 9820917HCID 9820917, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 1-(3,4-dichlorobenzenesulfonyl)-4,5,6,7-tetrahydroindole -2-carboxylate (66 mg) from Example 2d above and lithium iodide (228 mg) were dissolved in pyridine (5 ml) and heated at reflux for 5 hours, cooled, then concentrated in vacuo. The residue was partitioned between 2N HCl and ether. Combined organic extracts were dried (MgSO4), concentrated, and the residue triturated with ether to give the product as a white crystalline solid which was filtered and dried (18 mg, 28%), NMR d(DMSO) 1.65 (4H, m), 2.38 (2H, m), 2.80 (2H, m), 6.70 (1H, s), 7.90 (2H, m), 8.30 (1H, s); M/z (+) 373 (M-H+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between 2N HCl and ether
  6. dry with materialCombined organic extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. customthe residue triturated with ether

Sources & evidence

ORD record
ord-9245d3a8838a42628815539d48eb381b
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Reaction notes

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