Thiophosgene → 2-Ethyl-4-cyanophenyl isothiocyanate

HRID 276243

反応式

HRID 276243 の反応式
[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]

参加物

4

反応物 2

HCID 10040ThiophosgeneHCID 27353304-Amino-3-ethylbenzonitrile

生成物 1

HCID 183161022-Ethyl-4-cyanophenyl isothiocyanate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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)+).

後処理

  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

出典と根拠

ORDレコード
ord-b3db55aa994a4f63ac19e73ea3b366b8
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

関連ノート

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