Triethylamine → HCID 178485068, compound

HRID 1702473Notes

Reaction equation

HRID 1702473 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].C(N(CC)CC)C.[C:19]([NH:21][C:22](Cl)=[N:23][CH3:24])#[N:20]>CO>[C:19]([N:21]=[C:22]([NH:11][CH2:10][CH2:9][S:8][CH2:7][C:3]1[N:4]=[CH:5][NH:6][C:2]=1[CH3:1])[NH:23][CH3:24])#[N:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 12918610N-cyano-N'-methylchloroformamidine

Product 1

HCID 178485068HCID 178485068, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(5-methylimidazol-4-ylmethylthio)ethylamine (1.0 g) and triethylamine (0.71 g) in methanol (20 ml) was added N-cyano-N'-methylchloroformamidine (0.82 g) and stirred for 7.5 hrs. at 50°-55° C. After evaporation, the residue was subjected to chromatography on SiO2 [eluant: CHCl3 -MeOH (10:1)]. The resulting crude product was added to water (3 ml) and extracted repeatedly with ethyl acetate. Ethyl acetate extracts were dried over anhydrous MgSO4 and concentrated under a reduced pressure to small volume. The resulting crystals were collected by filtration and washed with ethyl acetate to give N"-cyano-N-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (0.33 g). Yield 22.4%, m.p. 134°-137° C.

Workup

  1. customat 50°-55° C
  2. customAfter evaporation
  3. additionThe resulting crude product was added to water (3 ml)
  4. extractionextracted repeatedly with ethyl acetate
  5. dry with materialEthyl acetate extracts were dried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure to small volume
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ab700c3708cf4166b010fdbf2e849a44
Source dataset
uspto-grants-1983_04
Patent number
US04381395

Reaction notes

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