Sodium Carbonate → 2-Bromo-4-thiocyanatoaniline

Reaction equation

[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[S-:9][C:10]#[N:11].[Na+].BrBr.[Br-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[Br:1][C:2]1[CH:8]=[C:7]([S:9][C:10]#[N:11])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

Reactant 5

HCID 10340Sodium Carbonate

HCID 119922-Bromoaniline

HCID 24408Bromine2×

HCID 253881Sodium Bromide

HCID 516871Sodium thiocyanate

Product 1

HCID 38124212-Bromo-4-thiocyanatoaniline

Reagents, catalysts & solvents 2

Procedure

To a cold (0°-5° C.), stirred solution of o-bromo-aniline (20.6 g., 0.12 mole) and sodium thiocyanate (29.2 g., 0.36 mole) in methanol (300 ml.) is added dropwise a solution of bromine (19.5 g., 0.122 mole) in methanol (75 ml.) saturated with sodium bromide. The solution is stirred for 1 hour following the addition of the bromine and then poured into water (2 liters) and neutralized with sodium carbonate. The resulting solid is collected, washed with water and dried, m.p. 74°-79° C.