HCID 86632907, compound → HCID 86632908, compound

HRID 1398907Notes

Reaction equation

HRID 1398907 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4]1[C:5]([NH2:14])=[C:6]([N+:11]([O-])=O)[C:7]([F:10])=[CH:8][CH:9]=1)[CH3:2]>[Pd].O1CCCC1>[CH2:15]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([NH2:11])[C:5]=1[NH2:14])[CH3:16]

Participants

4

Reactant 1

HCID 86632907HCID 86632907, compound

Product 1

HCID 86632908HCID 86632908, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under hydrogen gas atmosphere, a mixture of N1,N1-diethyl-4-fluoro-3-nitrobenzene-1,2-diamine (380 mg, 1.67 mmol), 10% palladium on carbon (50% wet, 80 mg) and tetrahydrofuran (8 mL) was stirred at room temperature for 20 hr. The reaction mixture was filtered and concentrated in vacuo to give N1,N1-diethyl-4-fluorobenzene-1,2,3-triamine as a brown oil, which was used for the next step without further purification. To a solution of above crude compound in tetrahydrofuran (16 mL) was added 2,4-dichlorophenyl isothiocyanate (320 mg, 1.57 mmol) at room temperature. The resultant mixture was stirred at room temperature for 2 h and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture to give a solid, which was washed with diisopropyl ether to afford the title compound as a colorless solid (306 mg, 0.762 mmol, 49%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cc5b312e0fe4b81bcde21bea9a34f78
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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