Ethanol → HCID 15514362, compound

HRID 705434Notes

Reaction equation

HRID 705434 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[N:6]=1.O.O.Cl[Sn]Cl.CCO.[OH-].[K+]>O>[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 12873106HCID 12873106, compound

Product 1

HCID 15514362HCID 15514362, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-methyl-4-(4-nitrophenyl)oxazole (J. Heteocyclic Chemistry, 1981, 885)(1.12 g, 5.48 mmol) was added to a refluxing solution of SnCl2.2H2O (6.33 g, 28.1 mmol), conc HCL (10 mL) and EtOH (20 mL). The reaction is stirred for 30 min then cooled to room temperature and poured into a solution of 24 g of KOH in 100 mL of water. The resulting mixture was cooled in an ice bath and stirred for an additional 30 min. The product was collected by filtration as a yellow solid (1.35 g, 83%). LC-MS (M+H): 191

Workup

  1. temperatureThe resulting mixture was cooled in an ice bath
  2. stirringstirred for an additional 30 min
  3. filtrationThe product was collected by filtration as a yellow solid (1.35 g, 83%)

Sources & evidence

ORD record
ord-c4a09259f7bd460eb7181373a7463ca0
Source dataset
uspto-grants-2015_11
Patent number
US09174949B2

Reaction notes

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