Methyl iodide → 4-(4-Hydroxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide

HRID 1169527노트

반응식

HRID 1169527 반응식
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH3:17])[C:7]=1[C:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]=1[CH3:16].[I:18][CH3:19]>CO>[I-:18].[OH:15][C:11]1[CH:12]=[C:13]([CH3:14])[C:8]([C:7]2[C:6]([CH3:17])=[CH:5][N+:4]([CH3:19])=[CH:3][C:2]=2[CH3:1])=[C:9]([CH3:16])[CH:10]=1

참가 물질

4

반응물 2

HCID 6328Methyl iodideHCID 1360343674-(3,5-Dimethyl-pyridin-4-yl)-3,5-dimethyl-phenol

생성물 1

HCID 669936364-(4-Hydroxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

To a stirring solution of 6 (0.113 g, 0.500 mmol) in anhydrous methanol (10 mL) was added dropwise iodomethane (0.5 mL, 0.660 g, 2.75 mmol) at room temperature under N2. The reaction mixture was then stirred at 60° C. under N2 overnight. After cooling to room temperature, the mixture was concentrated in vacuo to give the corresponding methyl pyridinium iodide salt as an analytically pure yellow solid (0.184 g, 99.4%). mp 257-258° C.; 1H NMR (500 MHz, DMSO-d6): δ 9.562 (s, 1H), 8.898 (s, 2H), 6.645 (s, 2H), 4.295(s, 3H), 2.015 (s, 6H), 1.760 (s, 6H); 13C NMR (125 MHz, DMSO-d6): δ 157.588, 157.448, 143.158, 136.942, 134.675, 124.179, 114.988, 47.297, 19.162, 16.527; MS (ESI): m/z 242.4 [(M−I)+, 100]; Anal. Calcd. For C16H20INO·H2O: C, 49.62; H, 5.73; N, 3.62; I, 32.77. Found: C, 50.08; H, 5.52; N, 3.65; I, 33.49.

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo

출처 및 근거

ORD 기록
ord-279712891ed94928b604bb9f9a98351e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07824582B2

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