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Bis(2-Methoxyethyl)amine → 2-bromo-N,N-bis(2-methoxyethyl)acetamide

HRID 45917
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HRID 45917 반응식
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][CH3:9].C(N(CC)CC)C.[Br:17][CH2:18][C:19](Br)=[O:20]>C(Cl)Cl>[Br:17][CH2:18][C:19]([N:5]([CH2:6][CH2:7][O:8][CH3:9])[CH2:4][CH2:3][O:2][CH3:1])=[O:20]
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참가 물질

5

반응물 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

생성물 1

HCID 108009062-bromo-N,N-bis(2-methoxyethyl)acetamide수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

To a stirred solution of DCM, bis(2-methoxyethyl)amine (40.0 g, 44.0 mL, 300 mmol), and triethylamine (69.25 mL, 500 mmol), under a nitrogen atmosphere at −78° C. was added drop wise bromo acetyl bromide (34.8 mL, 400 mmol). After stirring at −78° C. for 5 h, the reaction mixture was allowed to warm up to −20° C. and then quenched by addition of water (60 mL). The organic phase was washed with distilled water (3×30 mL), saturated ammonium chloride (3×30 mL), saturated sodium bicarbonate (3×30 mL) and brine (2×30 mL). The organic phase was then dried over magnesium sulfate, filtered and solvents removed via rotary evaporation to yield a crude product in 82% yield (62.3 g, 245 mmol). The crude product was then distilled under high vacuum at 170° C. to give pale yellow crystals in 49% yield (35.57 g, 140 mmol). Pure product can also be recrystallised from the crude material with diethyl ether.

후처리

  1. temperatureto warm up to −20° C.
  2. customquenched by addition of water (60 mL)
  3. washThe organic phase was washed with distilled water (3×30 mL), saturated ammonium chloride (3×30 mL), saturated sodium bicarbonate (3×30 mL) and brine (2×30 mL)
  4. dry with materialThe organic phase was then dried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvents removed via rotary evaporation

출처 및 근거

ORD 기록
ord-61514cbc193a4022a9a1df6e9869aacf
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541598B2

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