Ammonium Chloride → HCID 178478780, compound

HRID 1382763Notes

Reaction equation

HRID 1382763 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][C:14](=[NH:17])OC)[N:9]=1)[C:2]([NH2:4])=[NH:3].[Cl-:18].[NH4+:19]>C(O)C>[ClH:18].[ClH:18].[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][C:14]([NH2:17])=[NH:19])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 12881442Methyl 3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]propanimidate

Product 1

HCID 178478780HCID 178478780, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-(2-guanidino-4-thiazolylmethylthio)propionimidate (4.09 g), ammonium chloride (0.8 g) and ethanol (25 ml) were stirred at room temperature for 5 hours. The methanol was evaporated at reduced pressure and the residue was chromatographed on silica gel using a chloroform/methanol gradient elution. Fractions containing the main product (as shown by T.L.C.) were combined and the solvent evaporated at reduced pressure. The residue was treated with ethanol containing hydrochloric acid. Excess of solvent was evaporated at reduced pressure and the residue was crystallised from isopropanol to give 3-(2-guanidino-4-thiazolylmethylthio)propionamidine dihydrochloride, (1.63 g) m.p. 174.5°-176.5° C.

Workup

  1. customThe methanol was evaporated at reduced pressure
  2. customthe residue was chromatographed on silica gel using
  3. washa chloroform/methanol gradient elution
  4. additionFractions containing the main product (as shown by T.L.C.)
  5. customthe solvent evaporated at reduced pressure
  6. additionThe residue was treated with ethanol
  7. additioncontaining hydrochloric acid
  8. customExcess of solvent was evaporated at reduced pressure
  9. customthe residue was crystallised from isopropanol

Sources & evidence

ORD record
ord-5e3365274e104226984969c88662517b
Source dataset
uspto-grants-1989_02
Patent number
US04808589

Reaction notes

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