Thiophosgene → 2,3-Dimethyl-6-nitrophenyl isothiocyanate

HRID 276246Notes

Reaction equation

HRID 276246 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[C:13](Cl)(Cl)=[S:14]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[N:4]=[C:13]=[S:14]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 5971662,3-Dimethyl-6-nitroaniline

Product 1

HCID 183164822,3-Dimethyl-6-nitrophenyl isothiocyanateYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,3-dimethyl-6-nitroaniline (3.0 g, 1.0 equiv.) in toluene (150 mL) was added thiophosgene (2.5 mL, 1.8 equiv.) and the reaction mixture was heated at the reflux temp. overnight. The resulting mixture was concentrated under reduced pressure and the residue was purified by column chromatography (10% CH2Cl2/hex) to afford 2,3-dimethyl-6-nitrophenyl isothiocyanate as a light yellow solid (3.63 g, 95%): 1H NMR (CDCl3) δ2.39 (s, 3H), 2.40 (s, 3H), 7.17 (d, J=8.4 Hz, 1H), 7.83 (d, J=8.7 Hz, 1H).

Workup

  1. temperaturethe reaction mixture was heated at the reflux temp
  2. customovernight
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography (10% CH2Cl2/hex)

Sources & evidence

ORD record
ord-d2f4a7b7ae2442ffa1e58b485a373edd
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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