Triethylamine → 2,3-Dihydro-1,4-benzodioxin-6-yl isothiocyanate

HRID 5848

反応式

HRID 5848 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19](Cl)(Cl)=[S:20]>C1(C)C=CC=CC=1>[CH2:3]1[CH2:2][O:1][C:6]2[CH:7]=[CH:8][C:9]([N:11]=[C:19]=[S:20])=[CH:10][C:5]=2[O:4]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 891481,4-Benzodioxan-6-ylamine

生成物 1

HCID 27761732,3-Dihydro-1,4-benzodioxin-6-yl isothiocyanate収率 37.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
80 °C

実験手順

To a mixture of 1,4-benzodioxan-6-amine (15.1 g; 100 mmol) and triethylamine (20.2 g, 200 ml) in toluene (350 ml) was added dropwise over 10 min. thiophosgene (11.5 g, 100 mmol) in toluene (50 ml). The mixture was stirred at 80° C. for 30 min., cooled to room temperature and filtered. The filtrate was evaporated. The product was redissolved in toluene and concentrated in vacuo. The resulting oil was taken up in warm petroleum ether, which was filtered. The filtrate was concentrated to a small volume, which afforded 7.2 g of 3,4-ethylenedioxyphenylisothiocyanate. 3,4-Ethylenedioxyphenylisothiocyanate (1.1 g; 5.7 mmol) in toluene (15 ml) was added to 3-[4-(2-chlorophenyl)piperazin -1-yl]propylamine (1.45 g, 5.7 mmol) in toluene (45 ml). The mixture was refluxed for 6 h, cooled to room temperature and purified by column chromatography on silica gel 60 eluting with toluene graduated to toluene/ethyl acetate (1:1). The product was triturated with petroleum ether and redissolved in ethanol. Addition of hydrogen chloride in ether precipitated the title compound, which was recrystallized from ethanol to give 180 mg. M.p. 210°-212° C. MS (70 eV): m/z 447 (M+, 1%), 445 (1), 295 (4), 193 (100), 166 (10), 151 (20).

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. dissolutionThe product was redissolved in toluene
  5. concentrationconcentrated in vacuo
  6. filtrationwhich was filtered
  7. concentrationThe filtrate was concentrated to a small volume, which

出典と根拠

ORDレコード
ord-e06146ed2854458e91b224a994c85528
出典データセット
uspto-grants-1993_09
特許番号
US05246935

関連ノート

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