Cyanamide → HCID 178486952, compound

HRID 522480

Reaction equation

HRID 522480 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.[N:11]#[C:12][NH2:13]>Cl.O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12]([NH2:13])=[NH:11])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 9864CyanamideHCID 4592574-Bromo-2-methoxyaniline

Product 1

HCID 178486952HCID 178486952, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-bromo-2-methoxyaniline 7.1 g (35.1 mmol) in HCl 25% m/v 20 mL, cyanamide 20.6 g (494.3 mmol) was added in portion (1.6 g every half hour). The reaction was stirred at 60° C. for 6 hours, then cooled down to room temperature, diluted with H2O (20 mL), extracted with AcOEt (10 mL). NaOH 35% (30 mL) was added to pH>>14. The aqueous phase was extracted with AcOEt (3×50 mL), dried over Na2SO4 and concentrated to afford 8.5 g (quantitative yield) of the title compound.

Workup

  1. temperaturecooled down to room temperature
  2. extractionextracted with AcOEt (10 mL)
  3. additionNaOH 35% (30 mL) was added
  4. extractionThe aqueous phase was extracted with AcOEt (3×50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d6a4464abc364f4787907a8e4c53f034
Source dataset
uspto-grants-2016_05
Patent number
US09333205B2

Linked notes

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