Acetonitrile → HCID 178432738, 화합물

HRID 1672216노트

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HRID 1672216 반응식
[ClH:1].[CH3:2][N:3]([CH3:15])[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([NH2:14])[C:10]([CH3:13])=[N:11][CH:12]=1.C(#N)C.Cl.[Cl:20][C:21]([NH2:23])=[NH:22]>C(O)(=O)C>[ClH:20].[ClH:1].[ClH:20].[CH3:15][N:3]([CH3:2])[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([NH:14][C:21]([NH2:23])=[NH:22])[C:10]([CH3:13])=[N:11][CH:12]=1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 3084509Chloroformamidinium chlorideHCID 67336892HCID 67336892, 화합물

생성물 1

HCID 178432738HCID 178432738, 화합물수율 136.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
50 °C

실험 절차

A 1 L, three-neck, round-bottom flask equipped with an overhead stirrer, a reflux condenser, an N2 inlet tube, and a temperature probe was charged with 5-(3-(dimethylamino)propyl)-2-methylpyridin-3-amine hydrochloride (25 g, 0.109 mol). Acetonitrile (275 mL, 11 vol) was added to it followed by acetic acid (25 mL, 1 vol). The initial suspension turned into a clear solution after the addition of acetic acid. Chloroformamidine hydrochloride (15.6 g, 0.136 mol, 1.25 equiv) was added to the solution resulting in a suspension. The reaction was heated at 40° C. for 30 min and at 50° C. for another 30 min. Then the temperature was raised to 60° C. and the reaction was continued at this temperature. After 1-2 h at 60° C., the reaction mixture became turbid and after 3-4 h, solid started separating out. The reaction was continued at 60° C. for 20 h and was judged complete by LC-MS analysis. The reaction was cooled to ambient temperature and the solid was collected by filtration (N2 flow was used during the filtration). The filter cake was washed with acetonitrile (50 mL, 2 vol). The solid was dried under high vacuum overnight to obtain N-{5-[3-(Dimethylamino)propyl]-2-methylpyridin-3-yl}guanidine trihydrochloride (32.1 g, 85% recovery) as a light brown solid. Elemental analysis Calcd: C, 41.81; H, 7.02; Cl, 30.85; N, 20.32. Found: C, 41.09; H, 6.72; Cl, 31.51; N, 20.47; 1H NMR (500 MHz, D2O) δ ppm: 8.57 (s, 1H), 8.45 (s, 1H), 3.22-3.19 (m, 2H), 2.90 (t, 2H, J=10 Hz), 2.86 (s, 6H), 2.69 (s, 3H), 2.15-2.07 (m, 2H); ESI-MS m/z 236 (M+H, 100%).

후처리

  1. customA 1 L, three-neck, round-bottom flask equipped with an overhead stirrer, a reflux condenser, an N2 inlet tube
  2. customresulting in a suspension
  3. temperatureThen the temperature was raised to 60° C.
  4. waitafter 3-4 h
  5. customsolid started separating out
  6. waitThe reaction was continued at 60° C. for 20 h
  7. temperatureThe reaction was cooled to ambient temperature
  8. filtrationthe solid was collected by filtration (N2 flow
  9. filtrationwas used during the filtration)
  10. washThe filter cake was washed with acetonitrile (50 mL, 2 vol)
  11. customThe solid was dried under high vacuum overnight

출처 및 근거

ORD 기록
ord-45678a1eae2e4e18bbf28ff4ed927b33
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998952B2

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