Benzaldehyde → HCID 15524188、化合物

HRID 1530837ノート

反応式

HRID 1530837 の反応式
Cl.[Br:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH2:16])=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO.O.C([BH3-])#N.[Na+]>ClCCl>[Br:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH2:16])=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:8]2

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21253084HCID 21253084、化合物HCID 22242641Methanol--water (1/1)

生成物 1

HCID 15524188HCID 15524188、化合物収率 62.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of the product from Example 5 (1 g, 3.24 mmol) and benzaldehyde (0.71 mL, 7 mmol) in 2:1 MeOH/H2O (50 mL) was treated with sodium cyanoborohydride (0.56 g, 9 mmol) portionwise under nitrogen and stirred for six hours. The reaction mixture was then added to dichloromethane (150 mL) and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and activated charcoal, filtered through a plug of silica gel and concentrated under vacuum to dryness. The solids were triturated in hexane, filtered, and oven dried to give the title compound (0.73 g, 62% yield) as an orange solid, mp=150-152° C.

後処理

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried over magnesium sulfate and activated charcoal
  3. filtrationfiltered through a plug of silica gel
  4. concentrationconcentrated under vacuum to dryness
  5. customThe solids were triturated in hexane
  6. filtrationfiltered
  7. customoven dried

出典と根拠

ORDレコード
ord-e4038220c4ee48f7a70705b598cbbda0
出典データセット
uspto-grants-2001_03
特許番号
US06197771B1

反応ノート

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