Trifluoroacetic anhydride → 2,2,2-Trifluoro-N-[2-(4-nitro-phenyl)-ethyl]-acetamide

HRID 887667

반응식

HRID 887667 반응식
Cl.[N+:2]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][CH:6]=1)([O-:4])=[O:3].CCN(C(C)C)C(C)C.[O:23](C(C(F)(F)F)=O)[C:24]([C:26]([F:29])([F:28])[F:27])=O>C(Cl)Cl>[F:27][C:26]([F:29])([F:28])[C:24]([NH:11][CH2:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:13][CH:12]=1)=[O:23]

참가 물질

5

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)

생성물 1

HCID 64237442,2,2-Trifluoro-N-[2-(4-nitro-phenyl)-ethyl]-acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-nitrophenethylamine hydrochloride (50 g, 0.247 mole), DIEA (128 mL, 0.74 mole, 3 eq.) and CH2Cl2 (500 mL) in a 1 L round bottom flask equipped with a magnetic stirrer was added (CF3CO)2O (52.5 mL, 0.37 mole, 1.5 eq) dropwise at 5-10° C. (with ice/water bath). After stirring for another 1 h after the addition at RT, the reaction was quenched with water (200 mL) and transferred into a separatory funnel. The organic layer was separated, washed with water and sat. NH4Cl, dried over Na2SO4, filtered, concentrated to give a brown oil. The crude was triturated with water (300 mL), filtered and dried on vacuum overnight to give the desired 2,2,2-trifluoro-N-[2-(4-nitro-phenyl)-ethyl]-acetamide as a yellow solid. This can be used for next step without further purification. An analytical sample was obtained through recrystallization from CH3OH/H2O as a yellow solid.

후처리

  1. additionafter the addition at RT
  2. customthe reaction was quenched with water (200 mL)
  3. customtransferred into a separatory funnel
  4. customThe organic layer was separated
  5. washwashed with water and sat. NH4Cl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown oil
  10. customThe crude was triturated with water (300 mL)
  11. filtrationfiltered
  12. customdried on vacuum overnight

출처 및 근거

ORD 기록
ord-b1f2ea9aff9a4066930400f85f987c56
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247430B2

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