Thiophosgene → 2-Ethyl-4-cyanophenyl isothiocyanate

HRID 276243Notes

Reaction equation

HRID 276243 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH3:11].[C:12](Cl)(Cl)=[S:13]>C1(C)C=CC=CC=1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:1]=[C:12]=[S:13])=[C:3]([CH2:10][CH3:11])[CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 27353304-Amino-3-ethylbenzonitrile

Product 1

HCID 183161022-Ethyl-4-cyanophenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-amino-3-ethylbenzonitrile, (75 g, 0.51 mol) in toluene (1 L) was added thiophosgene, (43 mL, 0.56 mol, 1.1 equiv.) slowly via syringe. Within 5 min. a viscous slurry formed. The reaction mixture was heated to the reflux temp. and the viscosity diminished. The reaction mixture was heated at the reflux temp. for 5 h then allowed to cool to room temp. The resulting mixture was concentrated under reduced pressure and the residue was treated with CH2Cl2 (600 mL) and concentrated under reduced pressure to give 4-cyano-2-ethylphenyl isothiocyanate as a light tan crystalline solid (98 g, 100%): 1H NMR (DMSO-d6) δ1.18 (t, J=7.4 Hz, 3H), 2.69 (q, J=7.4 Hz, 2H), 7.55 (d, J=7.0 Hz, 1H), 7.75 (d, J=7.0 Hz, 2H), 7.84 (s, 1H); MS (CI-MS) m/z 189 ((M+H)+).

Workup

  1. customWithin 5 min. a viscous slurry formed
  2. temperatureThe reaction mixture was heated to the reflux temp
  3. temperatureThe reaction mixture was heated at the reflux temp
  4. concentrationThe resulting mixture was concentrated under reduced pressure
  5. additionthe residue was treated with CH2Cl2 (600 mL)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3db55aa994a4f63ac19e73ea3b366b8
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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