Triethylamine → 3,4,5-Trimethoxyphenyl isothiocyanate

HRID 5856

반응식

HRID 5856 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 1189003,4,5-Trimethoxyphenyl isothiocyanate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-586d8f67d54a4ce2aae6db63cc9c2cee
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246935

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