반응 #94852

ord-cdd4b4daba06472ea32bc0b00c8c0aaf

반응 방정식

N
ammonia
N=C(N)Nc1nc(C2CCCC(N)C2)cs1
2-guanidino-4-(3-aminocyclohexyl)thiazole
CSC(=N)N[N+](=O)[O-]
2-methyl-1-nitroisothiourea
O=C(O)/C=C\C(=O)O
maleic acid
N=C(N)Nc1nc(C2CCCC(NC(N)=N[N+](=O)[O-])C2)cs1.N=C(N)Nc1nc(C2CCCC(NC(N)=N[N+](=O)[O-])C2)cs1.O.O=C(O)/C=C\C(=O)O.O=C(O)/C=C\C(=O)O
2-guanidino-4-[3-(2-nitroguanidino)cyclohexyl] thiazole maleate hemihydrate

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The residue, obtained on evaporation of the reaction mixture
  2. 2
    세척Elution of the appropriate region of the chromatogram
  3. 3
    기타with hot ethanol and evaporation of the solvent
  4. 4
    기타gave a glass-like material

실험 절차

To a solution of 2-guanidino-4-(3-aminocyclohexyl)thiazole (0.3 g.) in ethanol (30 ml.) was added 2-methyl-1-nitroisothiourea (0.2 g.) and the mixture allowed to stand overnight at room temperature. The residue, obtained on evaporation of the reaction mixture, was subjected to preparative thin layer chromatography on silica gel GF plates (Uniplate, Analtech Inc. Delaware, USA) using chloroform:methanol:ammonia (s.g. 0.88) 80:20:0.5 v/v/v for development. Elution of the appropriate region of the chromatogram with hot ethanol and evaporation of the solvent gave a glass-like material. This was dissolved in a small volume of ethanol and the solution treated with a solution of maleic acid in acetone. The resulting solution was diluted with ether to give 2-guanidino-4-[3-(2-nitroguanidino)cyclohexyl] thiazole maleate hemihydrate (0.12 g.) which was obtained as an amorphous solid. The n.m.r. spectrum in d6 dimethylsulphoxide included resonances at 1.2 (brm), 1.8 (brm), 2.7 (m) 3.5(m) 6.11(s-maleic acid olefinic protons), 6.9(s), 8.05 (m) and 8.14 (brs).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04342765uspto-grants-1982_08