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

HRID 2065077Notes

Reaction equation

HRID 2065077 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:14][N:15]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[N:16]3)[S:12][CH:13]=2)OCC[O:5]1.Cl.[OH-].[Na+]>C1COCC1.O>[N+:20]([C:17]1[CH:18]=[CH:19][N:15]([CH2:14][C:11]2[S:12][CH:13]=[C:9]([C:4](=[O:5])[CH3:3])[N:10]=2)[N:16]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14798Sodium HydroxideHCID 669291444-(2-Methyl-[1,3]dioxolan-2-yl)-2-(3-nitro-pyrazol-1-ylmethyl)-thiazole

Product 1

HCID 669288151-[2-(3-Nitro-pyrazol-1-ylmethyl)-thiazol-4-yl]-ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-(2-methyl-[1,3]dioxolan-2-yl)-2-(3-nitro-pyrazol-1-ylmethyl)-thiazole (250 mg, 0.84 mmol) in THF (10.0 mL) was treated at 0° C. with HCl (2.5 mL of a 1M solution in water, 2.50 mmol). The reaction mixture was stirred at rt for 6 h. Water (10 mL) was added and the aqueous layer was set to pH 9-10 using 1M NaOH. The aq. layer was extracted with EA (2×10 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow solid. TLC: rf (19:1 CH2Cl2-MeOH)=0.25. LC-MS-conditions 02: tR=0.81 min; [M+H]+=253.06.

Workup

  1. extractionThe aq. layer was extracted with EA (2×10 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-93f340d78d3d465aaf04e37b36199609
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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