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

HRID 1919296노트

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HRID 1919296 반응식
[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]

참가 물질

6

반응물 4

HCID 1140Toluene2회HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

생성물 1

HCID 110637394-Isocyanato-2-(trifluoromethyl)benzonitrile

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b789babfc6c04d12a6b394a66f6847f2
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168627B2

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