tert-Butylsulfonamide → HCID 67174725、化合物

HRID 2096630ノート

反応式

HRID 2096630 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=O.[CH3:19][C:20]([S:23]([NH2:26])(=O)=[O:24])([CH3:22])[CH3:21]>C1COCC1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=[N:26][S:23]([C:20]([CH3:22])([CH3:21])[CH3:19])=[O:24]

参加物

5

反応物 2

HCID 2757335tert-ButylsulfonamideHCID 52705456-Bromoflavanone

生成物 1

HCID 67174725HCID 67174725、化合物収率 39%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 6-bromo-2-phenylchroman-4-one (2.010 g, 6.63 mmol) and 2-methyl-2-propane sulfonamide (804 mg, 6.63 mmol) in anhydrous THF (22 mL) is added Ti(OEt)4 (3.025 g, 2.80 mL, 13.22 mmol). The resulting mixture is heated to reflux for 20 h. Brine (10 mL) is added after the mixture is cooled to rt, and stirred vigorously for 10 min. The mixture is filtered through a pad of Celite, and washed with ethyl acetate (50 mL). The filtrate is washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue is purified through chromatography on silica gel to afford N-(6-bromo-2-phenylchroman-4-ylidene)-2-methylpropane-2-sulfinamide 1.05 g, 39%) as a light yellow solid. MS ESI +ve m/z 406 (M+H)+

後処理

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 20 h
  3. filtrationThe mixture is filtered through a pad of Celite
  4. washwashed with ethyl acetate (50 mL)
  5. washThe filtrate is washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified through chromatography on silica gel

出典と根拠

ORDレコード
ord-cd218a9a2df7404db084f7fc7d0e0283
出典データセット
uspto-grants-2013_05
特許番号
US08450308B2

反応ノート

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