Triethylene glycol monomethyl ether → 4-(2-(2-(2-Methoxyethoxy)ethoxy)ethoxy)phthalonitrile

HRID 39208

반응식

HRID 39208 반응식
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][OH:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9]

참가 물질

5

반응물 3

HCID 8178Triethylene glycol monomethyl etherHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

생성물 1

HCID 190655314-(2-(2-(2-Methoxyethoxy)ethoxy)ethoxy)phthalonitrile수율 45%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-nitrophthalonitrile (1.73 g, 10 mmol), triethylene glycol monomethyl ether (1.52 g, 10 mmol) and dried potassium carbonate (2.76 g, 20 mmol) in anhydrous DMF (15 mL) was stirred overnight at ambient temperature under argon. The solvents were removed in vacuo, and the crude product was purified by column chromatography on silica gel using dichloromethane/methanol mixture (97:3) as an eluent to give the product in 45% yield. [1H NMR (δ, ppm, CDCl3): 7.70 (d, 1H, J=8.7 Hz), 7.31 (d, 1H, J=2.5 Hz), 7.23 (dd, 1H, J=8.7 Hz, J=2.5 Hz), 4.22 (m, 2H), 3.88 (m, 2H), 3.6-3.75 (m, 6H), 3.53 (m, 2H), 3.37 (s, 3H).]

후처리

  1. customThe solvents were removed in vacuo
  2. customthe crude product was purified by column chromatography on silica gel
  3. customto give the product in 45% yield

출처 및 근거

ORD 기록
ord-128614155516453eb32cc2eb5f74fba1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524891B2

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