Sodium Carbonate → 4-Amino-2,3-dichlorophenyl thiocyanate

HRID 2120365Notes

Reaction equation

HRID 2120365 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[S-:10][C:11]#[N:12].[Na+].BrBr.[Br-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[Cl:1][C:2]1[C:8]([Cl:9])=[C:7]([S:10][C:11]#[N:12])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 118442,3-DichloroanilineHCID 24408BromineHCID 253881Sodium BromideHCID 516871Sodium thiocyanate

Product 1

HCID 146019304-Amino-2,3-dichlorophenyl thiocyanateYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a cold (0-5° C.) solution of 2,3-dichloroaniline (2 g) and sodium thiocyanate (3 g) in MeOH (30 ml), was added a solution of bromine (2 g) in MeOH (10 ml) saturated with sodium bromide. The solution was left to stir for 1 hour. The reaction mixture was poured into water (200 ml) and neutralised with sodium carbonate to pH 8. The solid was collected by filtration and dried to yield the title compound as a white solid (2.38 g) 88%. NMR: 6.35 (s, 2H), 6.81 (d, 1H), 7.55 (d, 1H); m/z (EI+): 218.

Workup

  1. waitThe solution was left
  2. filtrationThe solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-600422e8e40042edadd21a0ca46711ee
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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