Chloroform methanol → HCID 178503885, compound

HRID 66570Notes

Reaction equation

HRID 66570 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].C(Cl)(Cl)Cl.CO>CO>[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:5](=[N:1][C:2]#[N:3])[S:6][CH3:7])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 21584188Chloroform methanolHCID 1785126122-Guanidino-4-(3-aminocyclohexyl)thiazole

Product 1

HCID 178503885HCID 178503885, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 2-guanidino-4-(3-aminocyclohexyl)thiazole (0.25 g.) in methanol (10 ml.) was added dimethyl (cyanoimido)dithiocarbonate (0.15 g.) and the mixture allowed to stand overnight. The residue, obtained on evaporation of methanol, was subjected to preparative thin layer chromatography on silica gel GF (Uniplate, Analtech Inc., Delaware, USA) using chloroform/methanol (90:10 v/v) for development. Isolation of the appropriate region of the chromatogram and elution with warm ethanol/chloroform (50:50 v/v) and crystallisation of the material extracted from methanol ether gave 2-guanidino-4-[3-(3-cyano-2-methylisothioureido)-cyclohexyl]thiazole, m.p. 216°-218° (decomp.).

Workup

  1. washIsolation of the appropriate region of the chromatogram and elution
  2. customwith warm ethanol/chloroform (50:50 v/v) and crystallisation of the material
  3. extractionextracted from methanol ether

Sources & evidence

ORD record
ord-2a9c797881a042db87fa596828a7e654
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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