Lithium iodide → HCID 9863680, compound

HRID 1017736Notes

Reaction equation

HRID 1017736 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:16]([C:17]([O:19]C)=[O:18])=[CH:15][C:14]3[O:21][CH:22]=[CH:23][C:13]2=3)(=[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:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]3[O:21][CH:22]=[CH:23][C:13]2=3)(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 9885896HCID 9885896, compound

Product 1

HCID 9863680HCID 9863680, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 4-(3,4-dichlorobenzenesulfonyl)furo[3,2-b]pyrrole-5-carboxylate (1.15 g) and lithium iodide (4.0 g) were dissolved in pyridine (50 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 (0.58 g, 52%), NMR d(DMSO) 7.02 (1H, d), 7.27 (1H, s), 7.88 (2H, s), 8.03 (1H, d), 8.22 (1H, s); M/z (−) 360 (M+), 314, 252, 250, 227, 225, 209, 170. Analysis for C13H7Cl2NO5S found C, 43.2%; H, 2.1%; N, 3.8%; theory C, 41.4%; H, 2.0%; N, 3.9%.

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-1727559d20544f14a89c5fe4dadb37ff
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

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