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

HRID 393366Notes

Reaction equation

HRID 393366 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-bd04dc98f49b41f38d2df63e165da3de
Source dataset
uspto-grants-2004_10
Patent number
US06806367B2

Reaction notes

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