Water → 4-[2-[[3-(Trifluoromethyl)phenyl]amino]pyrimidin-4-yl]pyridine 1-oxide

HRID 724819Notes

Reaction equation

HRID 724819 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.ClC1C=CC=C(C(OO)=[O:32])C=1.O>C(Cl)Cl>[F:23][C:2]([F:22])([F:1])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][N+:19]([O-:32])=[CH:18][CH:17]=3)[CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 14347000N-(3-trifluoromethyl-phenyl)-4-pyridyl-2-pyrimidineamine

Product 1

HCID 105926524-[2-[[3-(Trifluoromethyl)phenyl]amino]pyrimidin-4-yl]pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.57 g (33.4 mmol) of N-(3-trifluoromethyl-phenyl)-4-pyridyl-2-pyrimidineamine are suspended in 200 ml of methylene chloride, and 10.49 g (33.42 mmol, 55% strength) of m-chloroperbenzoic acid are added. After 2 hours, 200 ml of water are added. The reaction product is isolated by filtration, washed with sodium carbonate solution and water and, after drying, N-(3-trifluoromethyl-phenyl)-4-(N-oxido-4-pyridyl)-2-pyrimidineamine is obtained. More product is obtained by chromatography (methylene chloride:methanol=9: 1) of the concentrated mother liquor; Rf =0.16 (methylene chloride:methanol=9:1).

Workup

  1. customThe reaction product is isolated by filtration
  2. washwashed with sodium carbonate solution and water
  3. customafter drying

Sources & evidence

ORD record
ord-2ecc2ddc46a348ec955370efeb8f18f2
Source dataset
uspto-grants-1998_01
Patent number
US05705502

Reaction notes

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