Thiophosgene → 2,3-Dimethyl-4-nitrophenyl isothiocyanate

HRID 276245Notes

Reaction equation

HRID 276245 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:5][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])=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:5][C:3]=1[N:4]=[C:13]=[S:14]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 70990352,3-Dimethyl-4-nitroaniline

Product 1

HCID 183160152,3-Dimethyl-4-nitrophenyl isothiocyanateYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,3-dimethyl-4-nitroaniline (0.5 g, 1.0 equiv.) in toluene (50 mL) was added thiophosgene (0.3 mL, 1.3 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 (25% CH2Cl2/hex) to afford 2,3-dimethyl-4-nitrophenyl isothiocyanate as a light yellow solid (0.30 g, 48%): 1H NMR (CDCl3) δ2.39 (s, 3H), 2.41 (s, 3H), 7.20 (d, J=8.4 Hz, 1H); CI-MS m/z 200 ((M+H)+).

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 (25% CH2Cl2/hex)

Sources & evidence

ORD record
ord-d72828e659f34340a7d8282e5173f795
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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