1,3-Dichloroacetone → 1-{[4-(Chloromethyl)-1,3-thiazol-2-yl]methyl}-4-methylpiperazine hydrochloride

HRID 2199673노트

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HRID 2199673 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9](=[S:11])[NH2:10])[CH2:4][CH2:3]1.[Cl:12][CH2:13][C:14]([CH2:16]Cl)=O.C(=O)(O)[O-].[Na+].S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[ClH:12].[Cl:12][CH2:13][C:14]1[N:10]=[C:9]([CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[S:11][CH:16]=1

참가 물질

6

반응물 4

HCID 107931,3-DichloroacetoneHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 246926242-(4-Methylpiperazin-1-yl)ethanethioamide

생성물 1

HCID 668386111-{[4-(Chloromethyl)-1,3-thiazol-2-yl]methyl}-4-methylpiperazine hydrochloride수율 107.2%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

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온도
60 °C

실험 절차

2-(4-Methylpiperazin-1-yl)ethanethioamide (0.438 g, 2.53 mmol), 1,3-dichloroacetone (0.355 g, 2.78 mmol) and sodium bicarbonate (0.236 g, 2.78 mmol) was stirred in chloroform (4 mL) at room temperature for 48 h. The reaction mixture was filtered and the filter cake was washed with chloroform. The filtrate was added dropwise to a cooled (ice bath) solution of thionyl chloride (0.205 mL, 2.78 mmol) in chloroform (2 mL). The solution was stirred at 60° C. for 0.5 h and then cooled to room temperature. The brown mixture was filtered and washed with chloroform to afford 1-{[4-(chloromethyl)-1,3-thiazol-2-yl]methyl}-4-methylpiperazine hydrochloride as a brown solid (0.421 g, 1.49 mmol, 59% yield). 1H NMR (400 MHz; D2O): 2.89 (s, 3H); 3.18-3.43 (m, 4H); 3.56-3.78 (m, 4H); 4.56 (s, 2H); 4.67 (s, 2H); 7.66 (s, 1H); MS (EI) for C10H16ClN3S: 246 (MH+).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with chloroform
  3. additionThe filtrate was added dropwise to
  4. temperaturecooled to room temperature
  5. filtrationThe brown mixture was filtered
  6. washwashed with chloroform

출처 및 근거

ORD 기록
ord-e11fae54703f42b5b87331392a1945ef
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359332B2

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