Sodium hydride → 2-{Hydroxy-[2-(4-methylpiperazin-1-yl)phenyl]-methyl}-thiomorpholin-3-one

HRID 411983

反応式

HRID 411983 の反応式
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][S:6][CH2:5][C:4]1=[O:9].[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[CH:19]=[O:20])[CH2:13][CH2:12]1>C1COCC1>[OH:20][CH:19]([C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[N:14]1[CH2:13][CH2:12][N:11]([CH3:10])[CH2:16][CH2:15]1)[CH:5]1[S:6][CH2:7][CH2:8][NH:3][C:4]1=[O:9]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 884021,4-Tetrahydrothiazine-3-oneHCID 27955662-(4-Methylpiperazin-1-yl)benzaldehyde

生成物 1

HCID 120830042-{Hydroxy-[2-(4-methylpiperazin-1-yl)phenyl]-methyl}-thiomorpholin-3-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (930 mg, 23.3 mmol of 60% oil dispersion) was washed with hexanes under a nitrogen atmosphere and suspended in 100 mL of anhydrous THF. Thiomorpholin-3-one (1.0 g, 8.55 mmol) was added, followed immediately by 2-(4-methylpiperazin-1-yl)-benzaldehyde (1.58 g., 7.75 mmol). The reaction was then heated to reflux overnight, cooled to room temperature and concentrated in vacuo. The residue was dissolved in methylene chloride and washed with aqueous ammonium chloride (NH4Cl) and saturated brine and then dried with MgSO4. Purification using flash chromatography gave 2-{hydroxy-[2-(4-methylpiperazin-1-yl)phenyl]-methyl}-thiomorpholin-3-one as a white solid, m.p. 137-139° C. Mass spectrum 322 (M+1).

後処理

  1. temperatureThe reaction was then heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with aqueous ammonium chloride (NH4Cl) and saturated brine
  6. dry with materialdried with MgSO4
  7. customPurification

出典と根拠

ORDレコード
ord-f157c392102844b2aaa45fa45e18f4a5
出典データセット
uspto-grants-2003_05
特許番号
US06562813B2

関連ノート

読み込み中…