Methanol → HCID 23144091, compound

HRID 337533Notes

Reaction equation

HRID 337533 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:13]=[CH:14][C:15](Cl)=[N:16][CH:17]=2)=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.[CH3:19][OH:20].C[O-].[Na+]>O1CCOCC1>[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:13]=[CH:14][C:15]([O:20][CH3:19])=[N:16][CH:17]=2)=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 23144666HCID 23144666, compound

Product 1

HCID 23144091HCID 23144091, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

2-Amino-5-(2-chloropyridin-5-yl)-4-(2-furyl)thiazole (2.22 g, 80.0 mmol) obtained in Step 1 and a methanol solution of 28% sodium methoxide (4.63 g, 24.0 mmol) were suspended in 1,4-dioxane (8 mL), followed by stirring at 95° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1) to afford 2-amino-4-(2-furyl)-5-(2-methoxypyridin-5-yl)thiazole (1.32 g, 60%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-92e87c61de3248e7bc96d63bd8e77c55
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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