Water → HCID 19775932, compound

HRID 1612571Notes

Reaction equation

HRID 1612571 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([O:11][C:12]2[CH:13]=[CH:14][C:15]([N+:19]([O-])=O)=[C:16]([CH:18]=2)[NH2:17])=[N:3]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([C:7]([F:9])([F:10])[F:8])=[CH:5][C:4]([O:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:19])=[C:16]([NH2:17])[CH:18]=2)=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 19775936HCID 19775936, compound

Product 1

HCID 19775932HCID 19775932, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The nitroaniline obtained in step A (2 g, 6.6 mmol) was dissolved in 50% aqueous ethanol (100 cm3) and sodium dithionite (4.61 g 26.5 mmol) added portionwise over 20 minutes to the stirred solution, each portion being allowed to dissolve before adding the next. The reaction mixture was heated under reflux with stirring for 1.5 hours and after cooling was poured into water (50 cm3) and neutralised with aqueous sodium bicarbonate before being extracted with ethyl acetate (2×100 cm3). The combined extracts were dried (MgSO4) and the solvent removed in vacuo leaving a light brown solid which was triturated with hexane, filtered and dried, to give 4-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)-o-phenylenediamine m.p. 109°-111° C.

Workup

  1. dissolutionto dissolve
  2. additionbefore adding the next
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux
  5. temperatureafter cooling
  6. extractionbefore being extracted with ethyl acetate (2×100 cm3)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customthe solvent removed in vacuo
  9. customleaving a light brown solid which
  10. customwas triturated with hexane
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-112f5511a3744436bf3d44eb0ced62d9
Source dataset
uspto-grants-1993_03
Patent number
US05190574

Reaction notes

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