Thiophosgene → 2-Ethyl-4-cyanophenyl isothiocyanate

HRID 276243노트

반응식

HRID 276243 반응식
[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]

참가 물질

4

반응물 2

HCID 10040ThiophosgeneHCID 27353304-Amino-3-ethylbenzonitrile

생성물 1

HCID 183161022-Ethyl-4-cyanophenyl isothiocyanate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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)+).

후처리

  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

출처 및 근거

ORD 기록
ord-b3db55aa994a4f63ac19e73ea3b366b8
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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