Triethylamine → 3,4,5-Trimethoxyphenyl isothiocyanate

HRID 5856

反応式

HRID 5856 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[C:14](Cl)(Cl)=[S:15].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:13][O:12][C:8]1[CH:7]=[C:5]([N:6]=[C:14]=[S:15])[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 322853,4,5-Trimethoxyaniline

生成物 1

HCID 1189003,4,5-Trimethoxyphenyl isothiocyanate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 3,4,5-trimethoxyaniline (440 mg; 2.4 mmol) in toluene (20 ml), thiophosgene (300 mg; 2.5 mmol) and triethylamine (500 mg; 5 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4,5-trimethoxyphenylisothiocyanate. To the crude product was added 3-[4-(4-chlorophenyl)-1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (40 ml) and refluxed for 16 h. The solvent was evaporated and the residue resuspended in ethyl acetate filtered and evaporated to dryness. The residue was submitted to flash chromatography on silica gel 60 eluting with toluene/ethyl acetate (1:1). The product was taken up in ethanol, which was treated with hydrogen chloride in ether to give 200 mg of the title compound. M.p. 172°-173° C. MS (70 eV): m/z 479 (M+, 0.1%), 254 (55), 225 (100), 209 (80), 182 (32).

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-586d8f67d54a4ce2aae6db63cc9c2cee
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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