Sodium Bicarbonate → HCID 67354698、化合物

HRID 2220159ノート

反応式

HRID 2220159 の反応式
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3]1.C(=O)([O-])O.[Na+].Cl[O-].[Na+]>C(Cl)Cl.CC1(C)N(OC)C(C)(C)CCC1>[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3]1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 62917126HCID 62917126、化合物

生成物 1

HCID 67354698HCID 67354698、化合物収率 85%

試薬・触媒・溶媒 2

HCID 50747681-Methoxy-2,2,6,6-tetramethylpiperidine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

4-[(3-hydroxy-1-pyrrolidinyl)sulfonyl]benzonitrile 23a (17.0 g, 67.3 mmol) was dissolved in DCM (300 ml) and treated at room temp with PS-TEMPO (capacity: 1.17 mmol/g, 400 mg, 0.74 mmol). Then 5% aqueous sodium hydrogencarbonate solution (150 ml) was added and the mixture stirred vigorously while cooling to 10° C. Aqueous sodium hypochlorite (titrated at 7.0 wt % NaOCl*; 77.6 ml, 93.0 g, 87.5 mmol) was added over 40 min, maintaining the temperature below 10° C. Cooling was removed and the reaction mixture stirred vigorously. TLC after 2 h showed no starting material, therefore the stirring was stopped and layers separated. The aqueous layer was extracted with DCM (2×30 ml), and the combined organic layers washed with saturated aqueous sodium thiosulphate (75 ml) then water (150 ml). Each of these aqueous layers were back-extracted with DCM (30 ml) and combined with the main organic extract, which was then filtered through a cotton wool plug and evaporated to dryness, yielding 14.3 g (85%) ketone 4-[(3-oxo-1-pyrrolidinyl)sulfonyl]benzonitrile 23b.

後処理

  1. temperaturemaintaining the temperature below 10° C
  2. temperatureCooling
  3. customwas removed
  4. stirringthe reaction mixture stirred vigorously
  5. customlayers separated
  6. extractionThe aqueous layer was extracted with DCM (2×30 ml)
  7. washthe combined organic layers washed with saturated aqueous sodium thiosulphate (75 ml)
  8. extractionEach of these aqueous layers were back-extracted with DCM (30 ml)
  9. filtrationwas then filtered through a cotton wool plug
  10. customevaporated to dryness

出典と根拠

ORDレコード
ord-aecfeadb0cb9498a8b789943b837ee6d
出典データセット
uspto-grants-2008_08
特許番号
US07417058B2

反応ノート

読み込み中…