Amidinothiourea → HCID 178428480, compound

HRID 1059906

Reaction equation

HRID 1059906 reaction equation
Cl[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][N:6]=1)=O.[C:13]([NH2:19])([NH2:18])=[N:14][C:15]([NH2:17])=[S:16]>C(O)C>[NH:14]([C:15]1[S:16][C:2]([CH3:12])=[C:3]([C:5]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][N:6]=2)[N:17]=1)[C:13]([NH2:19])=[NH:18]

Participants

4

Reactant 2

HCID 2724563AmidinothioureaHCID 186674842-Chloro-1-(4-methylpyridin-2-yl)propan-1-one

Product 1

HCID 178428480HCID 178428480, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-1-(4-methylpyridin-2-yl)propan-1-one (0.4 g) in ethanol (5 ml) was added 2-imino-4-thiobiuret (257 mg). The mixture was refluxed for 2 hours, and the solvent was evaporated under reduced pressure. To the residue were added ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution. The ethyl acetate layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, dichloromethane:methanol:triethylamine=80:10:1) to give 2-guanidino-5-methyl-4-(4-methylpyridin-2-yl)thiazole (402 mg).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the residue were added ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography (silica gel 25 g, dichloromethane:methanol:triethylamine=80:10:1)

Sources & evidence

ORD record
ord-9da09301d0ea4e07ab4d8449da8eb08b
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Linked notes

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