Toluene → 2-chloro-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-4(3H)-pyrimidinone

HRID 393363Notes

Reaction equation

HRID 393363 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[CH:6][C:5]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[NH:20][C:19]2=O)=[C:4]([F:30])[CH:3]=1.P(Cl)(Cl)([Cl:33])=O.C(N(CC)CC)C.C1(C)C=CC=CC=1>O>[Cl:33][C:19]1[N:18]([C:5]2[CH:6]=[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:15]([O-:17])=[O:16])[C:2]([Cl:1])=[CH:3][C:4]=2[F:30])[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[N:20]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 184029813-[4-Chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 102386332-chloro-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-4(3H)-pyrimidinoneYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione(4.5 g, 0.01 mol), phosphorus oxychloride(1.5 g, 0.01 mol), triethylamine(2.0 g, 0.02 mol) and toluene(14 ml) was heated under reflux for 24 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate solution contained 3.5 g(yield 76%) of the above compound III-1(HPLC analysis). The ethyl acetate solution was concentrated and purified by column chromatography on silica gel(20% ethyl acetate/hexane) to give compound III-1 as a white solid, m.p.128-131° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-ca32bfc0c75c43ecb2529bb48b5c8519
Source dataset
uspto-grants-2004_10
Patent number
US06806367B2

Reaction notes

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