Aniline → N,N-Di(6-hydroxyhexyl)aniline

HRID 1767165노트

반응식

HRID 1767165 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]>C(O)CCC>[OH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6115AnilineHCID 748286-Chloro-1-hexanol

생성물 1

HCID 21982671N,N-Di(6-hydroxyhexyl)aniline수율 70%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

Using a modified literature method (Moon, K.-J.; Shim, H.-K.; Lee, K.-S.; Zieba, J.; Prasad, P. N. Macromolcules 1996, 29, 861), the reaction of aniline with 6-chloro-1-hexanol in butanol provided N,N-bis(6-hydroxyhexyl)-aniline in 70% yield. A 100 mL two-necked flask containing 15 mL of dry DMF was cooled down to 0° C. with an ice bath. To this solution, 4.7 g (30.7 mmol) of phosphorous oxychloride was added dropwise and the mixture was stirred for 30 min at 0° C. 3 g (10.2 mmol) of N,N-bis(6-hydroxyhexyl)-aniline in dry DMF (15 mL) was added to the above solution and heated to 90° C. for 2 hrs. The reaction solution was cooled down to room temperature, poured into ice water and neutralized to pH 6-8 with saturated sodium hydroxide aqueous solution. The resulting solution was extracted with methylene chloride and then dried over magnesium sulfate. The crude compound was purified by silica gel column chromatography (ethyl acetate/hexane=1:5) to yield 2.3 g (63%) of pure light brown oil, (9). 1H-NMR (200 MHz, CDCl3): δ 9.71 (s, 1H, —CHO), 7.71 (d, 2H, J=9.0 Hz), 664 (d 2H, J=9.0 Hz), 3.55 (t, 4H, —CH2Cl, J=6.6 Hz), 3.35 (t, 4H, —NCH2—, J=7.6 Hz), 1.80 (m, 4H), 1.68-1.37 (m, 12H). 13C-NMR (100 MHz, CDCl3): δ 190.2, 152.7, 132.5, 124.9, 110.9, 51.1, 45.2, 32.7, 27.2, 26.9, 26.5. HRMS (EI): m/z=357.1617 (M+), Δ=2.6 ppm.

출처 및 근거

ORD 기록
ord-94f43311645346888961b0b3ca7f5a1d
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07232913B2

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