Hydrochloric Acid → 1-[2-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-thiazol-4-yl]-ethanone

HRID 2040031Notes

Reaction equation

HRID 2040031 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:14][N:15]3[N:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[N:16]3)[S:12][CH:13]=2)OCC[O:5]1.Cl.[OH-].[Na+]>C1COCC1>[N+:20]([C:18]1[CH:17]=[N:16][N:15]([CH2:14][C:11]2[S:12][CH:13]=[C:9]([C:4](=[O:5])[CH3:3])[N:10]=2)[N:19]=1)([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14798Sodium HydroxideHCID 671276452-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole

Product 1

HCID 671276681-[2-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-thiazol-4-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole (2.360 g, 7.94 mmol) in THF (40.0 mL) was treated with 1N HCl (21.4 mL, 21.4 mmol) and the reaction mixture was stirred at rt overnight. The reaction mixture was neutralized with 1N NaOH. The aq. layer was extracted twice with EA (20 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (6:4 hept-EA) gave the title compound as a yellow solid: TLC:rf (6:4 hept-EA)=0.29. LC-MS-conditions 02: tR=0.81 min, [M+H]+=254.35.

Workup

  1. extractionThe aq. layer was extracted twice with EA (20 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (6:4 hept-EA)

Sources & evidence

ORD record
ord-f01c301eeb044b92aea03647e5233467
Source dataset
uspto-grants-2013_11
Patent number
US08580831B2

Reaction notes

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