Sodium Dithionite → HCID 67074341, compound

HRID 1852398Notes

Reaction equation

HRID 1852398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=3[F:24])[C:10]=2[N+:25]([O-])=O)=[CH:4][C:3]=1[NH:28][S:29](=[O:32])(=[O:31])[NH2:30].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[NH2:25][C:10]1[C:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=2[F:24])=[CH:12][C:13]([F:15])=[CH:14][C:9]=1[O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:28][S:29](=[O:31])(=[O:32])[NH2:30])[CH:4]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 67073745HCID 67073745, compound

Product 1

HCID 67074341HCID 67074341, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

597 mg crude N-(2-fluoro-5-{5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]-2-nitrophenoxy}phenyl)sulfuric diamide (1.028 mmol, 1 eq.) were dissolved in 20 mL THF, warmed to 50° C., treated with a solution of 3.044 g sodium dithionite (17.484 mmol, 17 eq.) in 16 ml of water dropwise over a period of 30 minutes. The resulting mixture was stirred at this temperature for another 5 h. Upon cooling to rt the phases separated. The organic layer was separated, concentrated in vacuo and redissolved in ethyl acetate. The aqueouse layer was diluted with saturated sodium bicarbonate solution and then extracted twice with ethyl acetate. The combined organic layers were washed once with half saturated brine and once with brine saturated, dried, filtered and concentrated in vacuo, providing 547 mg of crude product which was used in the subsequent transformations without further purification.

Workup

  1. temperatureUpon cooling to rt the phases
  2. customseparated
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. dissolutionredissolved in ethyl acetate
  6. additionThe aqueouse layer was diluted with saturated sodium bicarbonate solution
  7. extractionextracted twice with ethyl acetate
  8. washThe combined organic layers were washed once with half saturated brine and once with brine saturated
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be5f64a124704c65954ffe65cad6f2d2
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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