Sodium Hydroxide → HCID 21272041, compound

HRID 1193483Notes

Reaction equation

HRID 1193483 reaction equation
[N:1]([O-])=O.[Na+].[ClH:5].[F:6][C:7]([F:18])([F:17])[CH2:8][O:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12].[OH-].[Na+]>O.Cl.C(OCC)(=O)C.CCOCC>[ClH:5].[F:6][C:7]([F:17])([F:18])[CH2:8][O:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][NH2:1]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 21272058HCID 21272058, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21272041HCID 21272041, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolvent3×HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium nitrite (11.7 g, 0.17 mol) in 25 mL water was added dropwise to a cold stirred mixture of 2-(2,2,2-trifluoroethoxy)aniline hydrochloride (33.7 g, 0.15 mol), concentrated HCl (53 mL) and water (25 mL) so that the temperature remained at -5° to -3° C. After the additio was complete, a solution of stannous chloride dihydrate (71.7 g, 0.32 mol) in 122 mL 6N HCl was added over a 1 hour period. After 0.5 hour at 0° C. the reaction was allowed to warm to room temperature. Stirring was continued for 24 hours, the reaction diluted with water, ethyl acetate (400 mL) added, cooled and made alkaline using 50% NaOH. The phases were separated and the organic phase washed with water, dried (MgSO4), filtered and concentrated to give an oil. The oil was dissolved in ether and treated with ethereal HCl. The resulting precipitated solid was collected and dried to give 26.4 g (73%) of 2-(2,2,2-trifluoroethoxy)phenylhydrazine hydrochloride, m.p. 168°-170° C.

Workup

  1. customremained at -5° to -3° C
  2. stirringStirring
  3. waitwas continued for 24 hours
  4. additionadded
  5. temperaturecooled
  6. customThe phases were separated
  7. washthe organic phase washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give an oil
  12. customThe resulting precipitated solid
  13. customwas collected
  14. customdried

Sources & evidence

ORD record
ord-a1c1deb756cc4f8cb4fff3d236930940
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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