Sodium Dithionite → HCID 86669371, compound

HRID 574096Notes

Reaction equation

HRID 574096 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([F:10])=[C:4]([N+:11]([O-])=O)[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C.O>[F:10][C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([F:1])=[C:3]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[F:22])[C:4]=1[NH2:11]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 86669363HCID 86669363, compound2×

Product 1

HCID 86669371HCID 86669371, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2,5-difluoro-N-(2-fluoro-4-iodophenyl)-3-methoxy-6-nitrobenzenamine (Intermediate 15, 565 mg, 1.3 mmol) in ethanol (12 mL) was stirred at 70° C. to obtain a clear solution. To this hot solution was dropwise added a freshly prepared solution of Na2S2O4 (695 mg, 3.9 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 Na2SO4 and concentrated to yield 3,6-difluoro-N1-(2-fluoro-4-iodophenyl)-5-methoxybenzene-1,2-diamine (320 mg). 1H-NMR (400 MHz, CDCl3): δ 3.60 (2H, bs), 3.82 (3H, s), 5.41 (1H, bs), 6.23-6.27 (1H, m), 6.68-6.73 (1H, m), 7.23 (1H, s), 7.38 (1H, d, J=10.8).

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 Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-659f8fcf7acd4c0ca8762c8ca92fbc98
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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