Thiophosgene → 5-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrile

HRID 1504946노트

반응식

HRID 1504946 반응식
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15](Cl)(Cl)=[S:16]>C1COCC1.O>[F:10][C:9]1[C:2]([N:1]=[C:15]=[S:16])=[CH:3][C:4]([C:11]([F:14])([F:12])[F:13])=[C:5]([CH:8]=1)[C:6]#[N:7]

참가 물질

5

반응물 2

HCID 10040ThiophosgeneHCID 682929284-Amino-5-fluoro-2-(trifluoromethyl)benzonitrile

생성물 1

HCID 867118105-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrile수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the compound 25 (660 mg, 3.25 mmol) in THF (6 mL) was added a solution of thiophosgene (1 mL, 13 mmol) in water (1 mL) slowly at room temperature. The reaction mixture was stirred for 1 h, then concentrated in vacuo. The residue was diluted with H2O. The aqueous solution was extracted with ethyl acetate. The organic layers were combined and washed with aq.NaHCO3 and brine, dried over Na2SO4, filtered and concentrated to provide the title compound 3d (700 mg, 88%) as a light yellow solid, which was used directly in next step without further purification. 1H NMR (400 MHz, CDCl3) δ7.63 (d, 1H, J=8.5 Hz), 7.57 (d, 1H, J=6.9 Hz).

후처리

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washwashed with aq
  5. dry with materialNaHCO3 and brine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b503dfbe286947bc9b160b8fa3abac6f
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216957B2

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