Potassium Carbonate → 3-(2-Oxopyrrolidin-1-yl)-4-phenoxy-5-sulfamoylbenzoic acid

HRID 1706801Notes

Reaction equation

HRID 1706801 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([S:24](=[O:27])(=[O:26])[NH2:25])[C:16]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]([OH:13])=[O:12])=[O:6].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([S:24](=[O:27])(=[O:26])[NH2:25])[C:16]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 3219633-(4-chlorobutanoylamino)-4-phenoxy-5-sulfamoylbenzoic acid

Product 1

HCID 203345293-(2-Oxopyrrolidin-1-yl)-4-phenoxy-5-sulfamoylbenzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound 3-(γ-chlorobutyrylamino)-4-phenoxy-5-sulfamylbenzoic acid (11.5 g) and anhydrous potassium carbonate (11.5 g) were slurried in dioxane (350 ml) and stirred under reflux overnight. The solvent was removed under reduced pressure and the residue taken up in a small volume of water. After acidification with 3 N acqueous HCl, the product separated as a gum. Methylene chloride was added and the mixture stirred for 1 hour. The product 3-(2-oxo-1-pyrrolidinyl)-4-phenoxy-5-sulfamylbenzoic acid, now in the form of a powder, was filtered, washed with water, and air-dried to give 7.5 g (61% on two steps). A sample was recrystallized from aq. dioxane to give colorless crystals with m.p. 282°-285°; ir (Nujol) 3400, 3250, 2600 (broad), 1735, 1660, 1600, and 1575 cm-1 ; nmr (d6 -DMSO) 1.2-2.3 (m, 4H), 3.41 (t, J=6, 2H), 6.7-7.5 (m, C6H5), 7.65 (s, SO2NH2), 8.15 (d, J=2, CH), and 8.46 ppm (d, CH); mass spectrum m/e 283 (100%) and 376 (M+).

Workup

  1. temperatureunder reflux overnight
  2. customThe solvent was removed under reduced pressure
  3. customAfter acidification with 3 N acqueous HCl, the product separated as a gum
  4. additionMethylene chloride was added
  5. stirringthe mixture stirred for 1 hour
  6. filtrationThe product 3-(2-oxo-1-pyrrolidinyl)-4-phenoxy-5-sulfamylbenzoic acid, now in the form of a powder, was filtered
  7. washwashed with water
  8. customair-dried
  9. customto give 7.5 g (61% on two steps)
  10. customA sample was recrystallized from aq. dioxane
  11. customto give colorless crystals with m.p. 282°-285°

Sources & evidence

ORD record
ord-5edec6a67a99496f9467da91b4577322
Source dataset
uspto-grants-1980_06
Patent number
US04208535

Reaction notes

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