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

HRID 1111782ノート

反応式

HRID 1111782 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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 3N acqueous HC1, 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+).

後処理

  1. temperatureunder reflux overnight
  2. customThe solvent was removed under reduced pressure
  3. customAfter acidification with 3N acqueous HC1, 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°

出典と根拠

ORDレコード
ord-a2162dbf715944e3856e868ad0b7e679
出典データセット
uspto-grants-1978_10
特許番号
US04118587

反応ノート

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