Phosgene → 6-Isocyanato-2,3-dihydro-1,4-benzodioxine

HRID 5851

反応式

HRID 5851 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:12](Cl)(Cl)=[O:13]>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:12]=[O:13])=[CH:10][C:5]=2[O:4]1

参加物

4

反応物 2

HCID 6371PhosgeneHCID 891481,4-Benzodioxan-6-ylamine

生成物 1

HCID 27761726-Isocyanato-2,3-dihydro-1,4-benzodioxine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 1,4-benzodioxan-6-amine (300 mg; 2.0 mmol) in toluene (20 ml) and phosgene (10 ml 20% in toluene; 19 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4-ethylenedioxyphenylisocyanate. The crude product was added 3-[4-(4-chlorophenyl)-1-piperazinyl]propanol (500 mg; 2.0 mmol) in toluene (10 ml) and refluxed for 16 h. The reaction mixture was then concentrated and submitted to flash chromatography on silica gel 60 eluting with toluene graduated to toluene/ethyl acetate (1:1). The product was taken up in ethyl acetate, which was treated with hydrogen chloride in ether. Recrystallization from methanol/ether afforded 440 mg of the title compound. M.p. 243°-244° C. MS (70 eV): m/z 431 (31%, M+), 254 (34), 209 (100), 177 (75), 121 (31), 70 (38).

後処理

  1. temperaturewas refluxed for 6 h
  2. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-14741824b5af4f6e81afacd2442b897f
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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