Ethanol → HCID 68163166, compound

HRID 574098Notes

Reaction equation

HRID 574098 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[C:14](F)[CH:13]=[C:12]([F:17])[C:11]=1[N+:18]([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH2:29]([OH:31])C>O>[F:17][C:12]1[CH:13]=[C:14]([O:31][CH3:29])[CH:15]=[C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])[C:11]=1[NH2:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 57625029HCID 57625029, compound2×

Product 1

HCID 68163166HCID 68163166, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2-fluoro-N-(3,5-difluoro-2-nitrophenyl)-4-iodobenzenamine (Intermediate 17, 550 mg, 1.35 mmol) in ethanol (12 mL) was stirred at 70° C. to obtain a clear solution. To this hot solution was added dropwise a freshly prepared solution of Na2S2O4 (707 mg, 4.0 mmol) in water (2 mL) and stirred the reaction mixture at 90° C. for 1 h. The progress of reaction was monitored by TLC. After completion, the reaction mixture was concentrated and residue dissolved in ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to yield 3-fluoro-N1-(2-fluoro-4-iodophenyl)-5-methoxybenzene-1,2-diamine (448 mg). 1H-NMR (400 MHz, CDCl3): δ 3.86 (3H, s), 6.43-6.50 (2H, m), 6.56-6.61 (1H, m), 7.26-7.27 (1H, m), 7.37 (1H, d, J=10.0).

Workup

  1. customto obtain a clear solution
  2. stirringstirred the reaction mixture at 90° C. for 1 h
  3. customThe progress of reaction
  4. concentrationAfter completion, the reaction mixture was concentrated
  5. dissolutionresidue dissolved in ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1e7fd5f0323a4e11a64ab8a1ff61d1c0
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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