Triethylamine → 2-bromo-N-isopropyl-N-phenyl-acetamide

HRID 482338노트

반응식

HRID 482338 반응식
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:18][CH2:19][C:20](Br)=[O:21]>Cl>[Br:18][CH2:19][C:20]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:21]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 13032N-IsopropylanilineHCID 61147Bromoacetyl bromide

생성물 1

HCID 152160012-bromo-N-isopropyl-N-phenyl-acetamide수율 99.8%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

Isopropyl aniline (8.00 g, 59.2 mmol) and triethylamine (8.26 mL, 59.2 mmol) are combined in anhydrousDCM (75 mL) under nitrogen and cooled to 0°-5° C. with an ice-water bath. Bromoacetyl bromide (5.16 mL, 59.2 mmol) is added dropwise over approximately 10 min. and the reaction is allowed to stir to ambient temperature overnight. The mixture is combined with aqueous HCl (50 mL 1N) and transferred to a separatory funnel. The organic layer is separated, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to provide the title compound as a brown solid (15.13 g, 59.1 mmol). 1H NMR (300 MHz, CDCl3) δ=1.08 (d, J=6.8 Hz, 6H); 3.53 (s, 2H); 4.92-5.01 (m, 1H); 7.18-7.54 (m, 5H). TLC Rf=0.22 (3:17 ethyl acetate: hexane).

후처리

  1. temperaturecooled to 0°-5° C. with an ice-water bath
  2. customtransferred to a separatory funnel
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-58e94c3485d949e7b39cb5c8eab421c5
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05795887

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