Benzaldehyde → HCID 15524188, 화합물

HRID 1106424노트

반응식

HRID 1106424 반응식
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

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21253084HCID 21253084, 화합물HCID 22242641Methanol--water (1/1)

생성물 1

HCID 15524188HCID 15524188, 화합물수율 62.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f93e578a7cf54e1da69895f8eaeda361
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057313

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