Triethylamine → HCID 178512348, compound

HRID 66572Notes

Reaction equation

HRID 66572 reaction equation
Cl.Cl.[NH:3]([C:7]1[S:8][CH:9]=[C:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH:14]([NH2:18])[CH2:13]2)[N:11]=1)[C:4]([NH2:6])=[NH:5].C(N(CC)CC)C.[N-:26]([C:29]#[N:30])[C:27]#[N:28].[Na+]>C(O)CCC>[NH:3]([C:7]1[S:8][CH:9]=[C:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:29]([NH2:30])=[N:26][C:27]#[N:28])[CH2:13]2)[N:11]=1)[C:4]([NH2:6])=[NH:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4350929Sodium dicyanamideHCID 178478795HCID 178478795, compound

Product 1

HCID 178512348HCID 178512348, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-guanidino-4-(3-aminocyclohexyl)thiazole dihydrochloride (0.62 g.), triethylamine (0.56 ml.) and sodium dicyanamide (0.23 g.) in n-butanol (10 ml.) was heated under reflux for four hours. The filtered reaction mixture was evaporated and the residue subjected to preparative thin layer chromatography on silica GF 254 (Merck) plates using chloroform/methanol/ammonia (s.g. 0.88) 8:2:03 v/v/v for development. Isolation of the appropriate region of the chromatogram and elution with hot ethanol/chloroform (50:50 v/v) gave 2-guanidino-4-[3-(2-cyanoguanidino)cyclohexyl] thiazole as a glass. The n.m.r. spectrum in d6 dimethylsulphoxide included resonances at 1.28(m); 1.8(m); 6.3(s); 6.55(br s); 6.67(d); 6.9(br s) and showed resonances attributable to solvation by ethanol (~0.5 mole) and water.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for four hours
  3. customThe filtered reaction mixture
  4. customwas evaporated
  5. washIsolation of the appropriate region of the chromatogram and elution with hot ethanol/chloroform (50:50 v/v)

Sources & evidence

ORD record
ord-cf765b2fb28148058387c46871181139
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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