Chloral Hydrate → HCID 87327711, compound

HRID 1619327Notes

Reaction equation

HRID 1619327 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].Cl[C:11](Cl)(Cl)[CH:12]([OH:14])O.[O-]S([O-])(=O)=O.[Na+].[Na+].[Cl-].[OH:25][NH3+:26]>Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:12](=[O:14])/[CH:11]=[N:26]/[OH:25])[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

7

Reactant 4

HCID 2707Chloral HydrateHCID 21645Hydroxylamine HClHCID 24436Sodium SulfateHCID 150201553-Bromo-5-fluoroaniline

Product 1

HCID 87327711HCID 87327711, compoundYield 111.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 3-bromo-5-fluoroaniline (4.0 g, 21.1 mmol, 1.0 equiv) in conc. HCl (10 mL) and water (100 mL) was heated until it became a clear solution. 2,2,2-trichloroethane-1,1-diol (3.83 g, 23.2 mmol, 1.1 equiv) and Na2SO4 (22.5 g, 158.5 mmol, 7.3 equiv.) was pre-warmed to 50° C. and added to the mixture. To the stirred mixture was then added an aqueous solution of hydroxylammonium chloride (4.39 g, 63.2 mmol, 3.0 equiv) dropwise. The resulting mixture was refluxed for 1 h. After it was cooled to room temperature, the precipitate was filtered and washed with excess water, dried under vacuum to provide 6.13 g of crude product, which was used into the next step without further purification. MS (ESI): 259, 261 (MH+).

Workup

  1. temperaturewas heated until it
  2. additionadded to the mixture
  3. temperatureThe resulting mixture was refluxed for 1 h
  4. filtrationthe precipitate was filtered
  5. washwashed with excess water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e38aa9d880284845852574f43b91defb
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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