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

HRID 244563ノート

反応式

HRID 244563 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

反応条件

温度
60 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-4dc5912a38b94ad68839327b7e0e8752
出典データセット
uspto-grants-2014_02
特許番号
US08658654B2

反応ノート

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