Hydrochloric Acid → 3-[4-Chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1017183Notes

Reaction equation

HRID 1017183 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[NH:11][C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1.Cl[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O>[Cl:1][C:2]1[C:7]([O:8][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[NH:11][C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 177702713-(4-chloro-2-fluoro-5-hydroxyphenyl)6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 184029813-[4-Chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (2.2 g), 2-chloronitrobenzene (1.3 g) and potassium carbonate (1.4 g) in N,N-dimethylformamide (100 ml) was heated at reflux for 3 hours under an atmosphere of nitrogen. The resulting mixture was poured into water (200 ml) and acidified by the addition of a small portion of conc. hydrochloric acid. The solution was extracted with a mixed solvent (ethyl acetate:hexane, 1:1,400 ml) and the organic phase dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue chromatographed on silica gel eluting with ethyl acetate:hexane, 1:1, to give 3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (Intermediate 11-18) as an amorphous solid (1.0-g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours under an atmosphere of nitrogen
  3. extractionThe solution was extracted with a mixed solvent (ethyl acetate:hexane, 1:1,400 ml)
  4. dry with materialthe organic phase dried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-2f613ea4f4324216a4feb0b0f588a95b
Source dataset
uspto-grants-2002_11
Patent number
US06479435B1

Reaction notes

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