Potassium Iodide → HCID 19007311, compound

HRID 1742687Notes

Reaction equation

HRID 1742687 reaction equation
[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][NH:19][CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2].[S:22]([C:26]1[CH:34]=[CH:33][C:29]([CH2:30][CH2:31]Cl)=[CH:28][CH:27]=1)(=[O:25])(=[O:24])[NH2:23].C(=O)(O)[O-].[Na+].[I-].[K+]>O.C(#N)C>[C:1]([C:4]([CH:17]1[CH2:21][CH2:20][N:19]([CH2:31][CH2:30][C:29]2[CH:28]=[CH:27][C:26]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:34][CH:33]=2)[CH2:18]1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium Bicarbonate2×HCID 6765244-(2-chloroethyl)benzenesulfonamideHCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 19007311HCID 19007311, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.3 g--see Preparation 8), 4-sulphamoylphenethyl chloride (0.23 g--see J. Pharm. Pharmacol., 16, 541, (1964)), sodium bicarbonate (0.4 g) and acetonitrile (10 ml) was heated under reflux for 2 hours. A further portion of sodium bicarbonate (1 g) was added followed by potassium iodide (0.2 g) and the mixture was heated under reflux for 2 hours. On cooling to room temperature, water (60 ml) was added and the mixture was extracted with dichloromethane (3×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a glass which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless foam, yield, 0.11 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2 hours
  5. extractionthe mixture was extracted with dichloromethane (3×50 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a glass which
  9. customwas purified by column chromatography on silica eluting with dichloromethane
  10. additioncontaining methanol (0% up to 10%)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4689002c38cb474c9e606a6412fdc48a
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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