Iodine → 3-Chloro-2-methyl-4-thiocyanatoaniline

HRID 81700

Reaction equation

HRID 81700 reaction equation
[S-:1][C:2]#[N:3].[NH4+].II.[Cl:7][C:8]1[C:9]([CH3:15])=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11].O>CO>[NH2:11][C:10]1[CH:12]=[CH:13][C:14]([S:1][C:2]#[N:3])=[C:8]([Cl:7])[C:9]=1[CH3:15]

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 68943-Chloro-2-methylanilineHCID 15666Ammonium thiocyanate

Product 1

HCID 378593093-Chloro-2-methyl-4-thiocyanatoanilineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of ammonium thiocyanate (1.61 g, 0.02 mol) and iodine (1.79 g, 7.1 mmol) in methanol was added 3-chloro-2-methylaniline (0.84 mL, 7.1 mmol) dropwise. The mixture was allowed to stir at room temperature for 2 days after which time water (50 mL) was added and the mixture was extracted with dichloromethane (4×50 mL). The extracts were washed with a 15% aqueous solution of sodium thiosulfate (100 mL) then dried (Na2SO4) and the solvent removed in vacuo to afford 4-amino-2-chloro-3-methylphenyl thiocyanate as a brown solid (1.26 g, 90%). Material was used crude in subsequent steps.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (4×50 mL)
  3. washThe extracts were washed with a 15% aqueous solution of sodium thiosulfate (100 mL)
  4. dry with materialthen dried (Na2SO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-18f328f8603c45858b6c51b22eb16fe8
Source dataset
uspto-grants-2014_09
Patent number
US08846704B2

Linked notes

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