Sodium Carbonate → 2-Bromo-4-thiocyanatoaniline

HRID 1065945Notes

Reaction equation

HRID 1065945 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-thiocyanatoanilineYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a cold (0°-5° C.), stirred solution of o-bromoaniline (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 one 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., yield 96% of theoretical.

Workup

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

Sources & evidence

ORD record
ord-c3b15695cbfd4b5c92e40906f7a10a57
Source dataset
uspto-grants-1982_05
Patent number
US04331817

Reaction notes

Loading…