Methanesulfonic Acid → HCID 18956305, compound

HRID 2379824Notes

Reaction equation

HRID 2379824 reaction equation
CS(O)(=O)=O.[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[N:10]=1)(=O)[CH3:7].BrBr.C(=O)([O-])O.[Na+].[NH2:28][C:29]([NH2:31])=[S:30]>O1CCOCC1.CO>[NH2:31][C:29]1[S:30][CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[N:10]=2)[N:28]=1

Participants

8

Reactant 5

HCID 6395Methanesulfonic AcidHCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 10375697HCID 10375697, compound

Product 1

HCID 18956305HCID 18956305, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Methanesulfonic acid (18.6 g) was added to a solution of 2-acetyl-6-(propionylaminomethyl)pyridine (40.0 g) in dioxane (800 ml) at room temperature. The mixture was stirred at room temperature for 15 minutes. Bromine (34.1 g) was added slowly to the mixture at room temperature. The mixture was heated at 50° C. for 3 hours. To the mixture sodium hydrogencarbonate (65.2 g), thiourea (17.7 g) and methanol (800 ml) was added. The mixture was heated at 50° C. for 4 hours. The solvent was removed under reduced pressure and the residue was dissolved in water (700 ml). The mixture was extracted with a mixture of ethyl acetate (700 ml) and tetrahydrofuran (700 ml). The extract was dried with magnesium sulfate and then was evaporated. The residue was crystallized from acetone to afford 2-amino-4-(6-propionylaminomethylpyridin-2-yl)thiazole (26.9 g).

Workup

  1. temperatureThe mixture was heated at 50° C. for 3 hours
  2. temperatureThe mixture was heated at 50° C. for 4 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in water (700 ml)
  5. extractionThe mixture was extracted with a mixture of ethyl acetate (700 ml) and tetrahydrofuran (700 ml)
  6. dry with materialThe extract was dried with magnesium sulfate
  7. customwas evaporated
  8. customThe residue was crystallized from acetone

Sources & evidence

ORD record
ord-8fd6e9ddd33d4e9b940a9004e6d49d06
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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