Hydrochloric Acid → HCID 21705086, compound

HRID 1595458Notes

Reaction equation

HRID 1595458 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20]([O:22]C)=[O:21])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[I-].[Li+].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20]([OH:22])=[O:21])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 21705077HCID 21705077, compound

Product 1

HCID 21705086HCID 21705086, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl N-(3-chlorophenylsulphonyl)indole-2-carboxylate (0.56 g) and lithium iodide (2.0 g) were dissolved in pyridine and heated at reflux for 6 hours, cooled to room temperature and poured into 2M HCl and extracted with diethyl ether. Combined organic extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography using DCM-2% methanol as eluent to give the desired product as a white solid (0.24 g, 45%), mp 216-217°; NMR δ (CD3SOCD3) 7.30-8.10 (m, 9H); M/z(−) 334 (M−H+), 290, 226, 191, 180, 116.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. extractionextracted with diethyl ether
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give an oil which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9b35214ddb20422cbd6a82939b5857fb
Source dataset
uspto-grants-2001_09
Patent number
US06288103B1

Reaction notes

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