Toluene → 4-Isocyanato-2-(trifluoromethyl)benzonitrile

HRID 1919296ノート

反応式

HRID 1919296 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[N:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:14](Cl)(Cl)=[O:15].C1(C)C=CC=CC=1.[OH-].[Na+]>C(OCC)(=O)C>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([C:12]#[N:13])=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1)=[C:14]=[O:15]

参加物

6

反応物 4

HCID 1140Toluene2 回HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

生成物 1

HCID 110637394-Isocyanato-2-(trifluoromethyl)benzonitrile

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 5-amino-2-cyanobenzotrifluoride (1a) (2.0 g, 10.7 mmol) in ethyl acetate (6 mL) at 0° C. under argon, was added dropwise a 2.0 M solution of phosgene in toluene (6.5 mL, 12.9 mmol). The solution was stirred 30 min at 0° C. and allowed to return at room temperature. Toluene (3 mL) was then added to the ethyl acetate and the resulting solution was refluxed for 3 hrs using a Dean-Stark apparatus, equipped with an HCl trap (solid NaOH). The first 6 mL of distilled solvent was removed and replaced by toluene (6 mL). The solution was then filtrated and evaporated to give compound 8a (1.6 g) as an orange oil which was directly used for the next step. IR: 2268 (strong), 2232 (weak) cm−1.

後処理

  1. customto return at room temperature
  2. temperaturethe resulting solution was refluxed for 3 hrs
  3. customThe first 6 mL of distilled solvent was removed
  4. filtrationThe solution was then filtrated
  5. customevaporated

出典と根拠

ORDレコード
ord-b789babfc6c04d12a6b394a66f6847f2
出典データセット
uspto-grants-2012_05
特許番号
US08168627B2

反応ノート

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