Potassium Hydroxide → N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide

HRID 719848

반응식

HRID 719848 반응식
[C:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([C:15]([F:18])([F:17])[F:16])[CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].C1C=C(C(O)=[O:26])C(C(OO)=O)=CC=1.[OH-].[K+]>C(OCC)(=O)C>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:1](=[O:5])[C:2]2([CH3:4])[O:26][CH2:3]2)=[CH:8][C:9]=1[C:15]([F:16])([F:17])[F:18])#[N:14]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 75329Monoperoxyphthalic acid2회HCID 11149469N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide

생성물 1

HCID 10149314N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide수율 77.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매3회

반응 조건

온도
80 °C

실험 절차

N-Methacryloyl-4-cyano-3-trifluoromethylaniline (13.8 g, 54 mmol) and ethyl acetate (40 ml) were charged in a 300 ml four-neck flask, and the mixture was heated at 50° C.–55° C. A solution of mono-perphthalic acid in ethyl acetate (108.05 g, net 19.82 g, 110 mmol) was added dropwise at a temperature in the range of 50° C.–55° C. over 3.9 hr. After stirring at the above-mentioned temperature for 4.5 hr, a solution of mono-perphthalic acid in ethyl acetate (10.36 g, net 1.90 g, 10.4 mmol) was further added dropwise over 10 min. Then the mixture was stirred for 1 hr and left standing overnight at room temperature. The mixture was adjusted to pH=8 (universal test paper) with 20% aqueous KOH solution and partitioned. The organic layer was washed with deionized water (20 ml) in which Na2S2O5 (5.0 g) had been dissolved, dried over MgSO4, decolorized with activated carbon (carborafine 0.5 g), and concentrated under reduced pressure. Toluene (60 ml) was added to the residue and the mixture was heated to 80° C. After cooling to 25° C., the mixture was filtrated to give 4-cyano-N-(2,3-epoxy-2-methylpropionyl)-3-trifluoromethylaniline (11.37 g, yield 77.3%). Purity 98.7%.

후처리

  1. temperaturethe mixture was heated at 50° C.–55° C
  2. stirringThen the mixture was stirred for 1 hr
  3. waitleft
  4. waitstanding overnight at room temperature
  5. custompartitioned
  6. washThe organic layer was washed with deionized water (20 ml) in which Na2S2O5 (5.0 g)
  7. dissolutionhad been dissolved
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. additionToluene (60 ml) was added to the residue
  11. temperatureAfter cooling to 25° C.
  12. filtrationthe mixture was filtrated

출처 및 근거

ORD 기록
ord-44f68c4632284b6891f3fb6addbeb0da
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132560B2

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