Cyanamide → HCID 178486952, compound
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- temperaturecooled down to room temperature
- extractionextracted with AcOEt (10 mL)
- additionNaOH 35% (30 mL) was added
- extractionThe aqueous phase was extracted with AcOEt (3×50 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d6a4464abc364f4787907a8e4c53f034
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09333205B2
Reaction notes
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