Tert-Butyl hypochlorite → 1-Chloro-3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one

HRID 1770726노트

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HRID 1770726 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[NH:13][C:12]1([CH3:20])[CH3:19].C(O[Cl:26])(C)(C)C>CO>[Cl:26][N:13]1[C:14]([CH3:18])([CH3:17])[C:15](=[O:16])[N:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:12]1([CH3:20])[CH3:19]

참가 물질

4

반응물 2

HCID 521297Tert-Butyl hypochloriteHCID 675080933-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one

생성물 1

HCID 569663761-Chloro-3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one수율 92%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

To a 0° C. solution of 3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one (15.03 g, 52.1 mmol) in methanol (150 ml) was added tert-butylhypochlorite (8.50 g of 0.91 g/mL, 78.3 mmol), over a 10 minute period. The mixture was stirred for 1 hour at 0° C. The reaction mixture was checked for completion by high pressure liquid chromatography. The reaction mixture was concentrated in vacuo, and crude material was purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane) to give 15.43 g (92%) of the title compound. 1H NMR (D2O, 400 MHz) δ 3.74-3.65 (m, 8H), 3.62-3.60 (m, 2H), 3.55 (t, J=6 Hz, 2H), 3.37 (s, 3H), 1.53 (s, 6H), 1.36 (s, 6H). 13C NMR (D2O, 100 MHz) δ 175.00, 83.68, 70.98, 69.59 (2 peaks), 69.39, 67.65, 66.02, 57.99, 40.16, 24.07, 22.52. LRMS (ESI/APCI) m/z 323 [M+H]+.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo, and crude material
  2. customwas purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-3f0a1a5932794f40a8809a35423c6bcb
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09248117B2

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