Methyl 3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]propanimidate → HCID 178512700, compound

HRID 1902234Notes

Reaction equation

HRID 1902234 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])[O:15]C)[N:9]=1)[C:2]([NH2:4])=[NH:3]>C(O)C.O>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][C:14]([NH2:17])=[O:15])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 1

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

Product 1

HCID 178512700HCID 178512700, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a mixture of 30 ml of ethanol and 30 ml of water was dissolved 5.0 g of methyl 3-(2-guanidinothiazol-4-ylmethylthio)propionimidate and after allowing to stand the solution for 20 hours at 40° C., the solvent was distilled off under reduced pressure. The residue formed was purified by a column chromatography using a mixture of chloroform and methanol and recrystallized from methanol to provide 3.2 g 3-(2-guanidinothiazol-4-ylmethylthio)propionamide showing a melting point of 193°-194° C. (decompd.).

Workup

  1. customfor 20 hours
  2. customat 40° C.
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue formed
  5. customwas purified by a column chromatography
  6. additiona mixture of chloroform and methanol
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e352c899ed3a4eb7837d05d02cd7bc0a
Source dataset
uspto-grants-1982_12
Patent number
US04362736

Reaction notes

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