Sodium Dithionite → HCID 67119849, compound

HRID 574095Notes

Reaction equation

HRID 574095 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([N+:21]([O-])=O)=[C:7]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:14]=2[F:20])[CH:8]=[C:9]([F:11])[CH:10]=1)[CH:2]=[CH2:3].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C.O>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:14]=2[F:20])[C:6]=1[NH2:21])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 67119633HCID 67119633, compound2×

Product 1

HCID 67119849HCID 67119849, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of N-(3-(allyloxy)-5-fluoro-2-nitrophenyl)-2-fluoro-4-iodobenzenamine (Intermediate 11, 1.56 g, 3.73 mmol) in ethanol (20 mL) was stirred at 70° C. to obtain a clear solution. To this hot solution was added dropwise a freshly prepared solution of Na2S2O4 (1.94 g, 11.19 mmol) in water (3.5 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 under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and concentrated to yield 3-(allyloxy)-5-fluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine (600 mg). 1H-NMR (400 MHz, CDCl3): δ 3.65 (2H, bs), 4.57 (2H, d, J=5.6), 5.32 (1H, d), 5.40 (1H, s), 5.46 (1H, d), 6.03-6.10 (1H, m), 6.45 (1H, dd, J=10.4, 2.8), 6.52 (1H, dd), 6.59 (1H, t) 7.27 (1H, d, J=9.2), 7.38 (1H, dd, J=10.4, 2).

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 under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3101ba05104443c5a0d2f8581d7a9d7c
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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