Ammonia → HCID 178512619, compound

HRID 66574Notes

Reaction equation

HRID 66574 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH2:16])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].CS[C:19](=[NH:24])[NH:20][N+:21]([O-:23])=[O:22].N.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]>C(O)C.CC(C)=O.CCOCC.CO.C(Cl)(Cl)Cl>[OH2:22].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:19]([NH2:24])=[N:20][N+:21]([O-:23])=[O:22])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:19]([NH2:24])=[N:20][N+:21]([O-:23])=[O:22])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]

Participants

10

Reactant 4

HCID 222AmmoniaHCID 444266Maleic AcidHCID 135927615N-Nitro-S-methylisothioureaHCID 1785126122-Guanidino-4-(3-aminocyclohexyl)thiazole

Product 1

HCID 178512619HCID 178512619, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

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).

Workup

  1. customThe residue, obtained on evaporation of the reaction mixture
  2. washElution of the appropriate region of the chromatogram
  3. customwith hot ethanol and evaporation of the solvent
  4. customgave a glass-like material

Sources & evidence

ORD record
ord-cdd4b4daba06472ea32bc0b00c8c0aaf
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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