Hydrochloric Acid → HCID 18667552, compound

HRID 1059881Notes

Reaction equation

HRID 1059881 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)=[C:5]([CH3:7])[N:6]=1.CS[C:17]1[S:18][CH2:19][CH2:20][N:21]=1.Cl.C(=O)([O-])O.[Na+]>COC(O)C.O1CCOCC1>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][C:17]2[S:18][CH2:19][CH2:20][N:21]=2)[S:3][C:4]=1[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 883244,5-Dihydro-2-(methylthio)thiazoleHCID 516892Sodium BicarbonateHCID 186309852-Amino-4-methyl-5-(4-methylpyridin-2-yl)-thiazole

Product 1

HCID 18667552HCID 18667552, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 30156371-MethoxyethanolSolvent

Procedure

To a suspension of 2-amino-4-methyl-5-(4-methylpyridin-2-yl)-thiazole and 2-(methylthio)-2-thiazoline (127 mg) in methoxyethanol (2 ml) was added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.23 ml). The mixture was refluxed for 20 hours, poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate twice. The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, 5% methanol in dichloromethane) and recrystallized from chloroform (1 ml)-diisopropyl ether (3 ml) to give 2-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-ylamino)-2-thiazoline (110 mg).

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 25 g, 5% methanol in dichloromethane)
  7. customrecrystallized from chloroform (1 ml)-diisopropyl ether (3 ml)

Sources & evidence

ORD record
ord-e7ef9cd76e19482bb0ebc62b6c60a001
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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