Formamide, N-(2-methylphenyl)- → 3-(2-Methylphenyl)-4,5-dimethylthiazolium chloride

HRID 1665445

반응식

HRID 1665445 반응식
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:12].[Cl:25][CH2:26][CH2:27][C:28](=O)[CH3:29].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[Cl-:25].[CH3:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:3]1[C:27]([CH3:26])=[C:28]([CH3:29])[S:12][CH:1]=1

참가 물질

7

반응물 4

HCID 7202Formamide, N-(2-methylphenyl)-HCID 10340Sodium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 806084-Chloro-2-butanone

생성물 1

HCID 674388643-(2-Methylphenyl)-4,5-dimethylthiazolium chloride수율 164.6%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 8b (4.055 g, 30 mmol) and phosphorus pentasulfide (1.351 g, 3.04 mmol) in dry 1,4-dioxane (4 mL) was stirred at room temperature for 15 min under an argon atmosphere. 4-Chloro-2-butanone (2.131 g, 20 mmol) was added and the resulting slurry was heated at 100° C. The reaction mixture was refluxed for 50 min, initially becoming clear yellow and finally deep red. After cooling at room temperature, the crude mixture was diluted with H2O (20 mL). Na2CO3 was added to the reaction mixture until pH≈7. The solvent was evaporated under reduced pressure and the resulting solid was suspended in CH2Cl2 and purified by column chromatography (column packed with silica gel) eluting with EtOH/CH2Cl2 (15/85). Upon concentration of the last yellowish band, a viscous orange oil was obtained. This was solidified when washed under vigorous stirring with diethyl ether (3×2 mL) to afford 9b as a tan solid (1.20 g, 17%). 1H NMR (CD2Cl2, 300 MHz): δ=11.09 (s, 1H), 7.53-7.31 (m, 4H), 2.57 (s, 3H), 2.08 (s, 3H), 2.04 (s, 3H); 13C{1H} NMR (CD2Cl2, 75 MHz): δ=160.77, 142.05, 136.10, 134.60, 134.30, 132.23, 132.00, 128.08, 126.55, 17.23, 12.90, 11.98; HRMS (FAB+) calculated for C12H14NS [M]+ 204.0847, observed 204.0845.

후처리

  1. temperaturethe resulting slurry was heated at 100° C
  2. temperatureThe reaction mixture was refluxed for 50 min
  3. temperatureAfter cooling at room temperature
  4. customThe solvent was evaporated under reduced pressure
  5. custompurified by column chromatography (column packed with silica gel)
  6. washeluting with EtOH/CH2Cl2 (15/85)
  7. customUpon concentration of the last yellowish band, a viscous orange oil was obtained
  8. washwashed
  9. stirringunder vigorous stirring with diethyl ether (3×2 mL)

출처 및 근거

ORD 기록
ord-5c6d2f0fad5d4f1c8ed39a4b2718318a
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039566B2

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