Sodium Carbonate → 2-Bromo-4-thiocyanatoaniline

HRID 2072589Notes

Reaction equation

HRID 2072589 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

8

Reactant 5

HCID 10340Sodium CarbonateHCID 119922-BromoanilineHCID 24408Bromine2×HCID 253881Sodium BromideHCID 516871Sodium thiocyanate

Product 1

HCID 38124212-Bromo-4-thiocyanatoaniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

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.

Workup

  1. customThe resulting solid is collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-f23bdee71512483495879e5ba291ad25
Source dataset
uspto-grants-1990_04
Patent number
US04913728

Reaction notes

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