三乙胺 → 3,4,5-三甲氧基异硫氰酸苯酯

HRID 5856

反应方程式

HRID 5856 反应方程式
[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]

参与物

5

反应物 3

HCID 8471三乙胺HCID 10040硫光气HCID 322853,4,5-三甲氧基苯胺

产物 1

HCID 1189003,4,5-三甲氧基异硫氰酸苯酯

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

实验过程

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).

后处理

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

来源与证据

ORD记录
ord-586d8f67d54a4ce2aae6db63cc9c2cee
来源数据集
uspto-grants-1993_09
专利号
US05246935

关联笔记

加载中…