Hydrochloric Acid → HCID 178512455, compound

HRID 1914757Notes

Reaction equation

HRID 1914757 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]([F:13])([F:12])[F:11])=[C:6]([NH2:8])[CH:7]=1.[N:14]#[C:15][NH2:16].Cl>CCO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]([F:11])([F:12])[F:13])=[C:6]([NH:8][C:15]([NH2:16])=[NH:14])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 27793675-Bromo-2-(trifluoromethoxy)aniline

Product 1

HCID 178512455HCID 178512455, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

To a suspension of 5-bromo-2-trifluoromethoxy-phenylamine (5.0 g, 19.5 mmol) in EtOH (15 mL), cyanamide (1.64 g, 39 mmol) dissolved in 5 mL of EtOH and 1 mL H2O, and HCl 37% (3.25 mL) diluted in 10 mL EtOH were added drop wise into the mixture under stirring. The mixture was refluxed for 72 h. The mixture was cooled down to room temperature, concentrated then diluted with water; NaOH 1N was added to basic pH and extracted several times with ethyl acetate, dried over sodium sulfate and concentrated to afford 5.2 g of the title compound (89% yield).

Workup

  1. additionwere added drop wise into the mixture
  2. temperatureThe mixture was refluxed for 72 h
  3. concentrationconcentrated
  4. additionthen diluted with water
  5. additionNaOH 1N was added to basic pH
  6. extractionextracted several times with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dab530143d9f4bcdbf4d43907b921ef6
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

Loading…