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-])=O)=[N:16]3)[S:12][CH:13]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:14][N:15]3[CH:19]=[CH:18][C:17]([NH2:20])=[N:16]3)[S:12][CH:13]=2)[O:8][CH2:7][CH2:6][O:5]1Participants
Conditions
- Temperature
- 75 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a 0.1M solution of 4-(2-methyl-[1,3]dioxolan-2-yl)-2-(3-nitro-pyrazol-1-ylmethyl)-thiazole (320 mg, 1.08 mmol), iron powder (183 mg, 3.24 mmol) and NH4Cl (292 mg, 5.40 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 75° C. for 60 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (10 mL) was added followed by 1N NaOH (10 mL). The aq. layer was extracted with CH2Cl2 (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 brown oil. LC-MS-conditions 01: tR=0.54 min; [M+H]+=266.97.
Workup
- filtrationThe reaction mixture was filtered while hot and
- concentrationconcentrated under reduced pressure
- additionCH2Cl2 (10 mL) was added
- extractionThe aq. layer was extracted with CH2Cl2 (2×10 mL)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
Sources & evidence
- ORD record
- ord-62d488c2fea1457c87d186fa06fdc6e4
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288419B2
Linked notes
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