Tetrahydrofuran → 3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-2-[(1-cyclopentylidene)aminooxy]-6-trifluoromethyl-4(3H)-pyrimidinone

HRID 393366노트

반응식

HRID 393366 반응식
Cl[C:2]1[N:7]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-:23])=[O:22])[C:11]([Cl:24])=[CH:10][C:9]=2[F:25])[C:6](=[O:26])[CH:5]=[C:4]([C:27]([F:30])([F:29])[F:28])[N:3]=1.[C:31]1(=[N:36][OH:37])[CH2:35][CH2:34][CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>O>[Cl:24][C:11]1[C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])=[CH:13][C:8]([N:7]2[C:6](=[O:26])[CH:5]=[C:4]([C:27]([F:30])([F:29])[F:28])[N:3]=[C:2]2[O:37][N:36]=[C:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:9]([F:25])[CH:10]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 14500Cyclopentanone, oximeHCID 102386332-chloro-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-4(3H)-pyrimidinone

생성물 1

HCID 226602383-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-2-[(1-cyclopentylidene)aminooxy]-6-trifluoromethyl-4(3H)-pyrimidinone수율 84.7%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 2-chloro-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-4(3H)-pyrimidinone(1.28 g, 0.0027 mol), cyclopentanone oxime(027 g, 0.0027 mol), potassium carbonate(0.38 g, 0.027 mol) and tetrahydrofuran(11 ml) was heated under reflux for 3 hours. The reaction mixture was poured into water, extracted with ethyl acetate, and washed with brine. The organic phase was dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel(20% ethyl acetate/hexane) to give compound II-3 (1.23 g, yield 84.7%) as a white amorphous solid, m.p.76-78° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel(20% ethyl acetate/hexane)
  8. customto give compound II-3 (1.23 g, yield 84.7%) as a white amorphous solid, m.p.76-78° C.

출처 및 근거

ORD 기록
ord-bd04dc98f49b41f38d2df63e165da3de
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06806367B2

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