Carbon Tetrachloride → 3-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzonitrile

HRID 426144Notes

Reaction equation

HRID 426144 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([CH3:18])[CH:17]=2)[CH:12]=[N:13]O)[C:5]([CH:19]([CH3:21])[CH3:20])=[C:4]([Cl:22])[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(#N)C.CCOCC>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([CH3:18])[CH:17]=2)[C:12]#[N:13])[C:5]([CH:19]([CH3:20])[CH3:21])=[C:4]([Cl:22])[N:3]=1

Participants

6

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 11776TriphenylphosphineHCID 725369653-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzaldehyde oxime

Product 1

HCID 596868583-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzonitrileYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (70) (4.4 g, 12.93 mmol) in acetonitrile (40 ml), was added triphenylphosphine (13.56 g, 51.73 mmol) and carbon tetrachloride (2.5 ml, 25.86 mmol). After 30 min., carbon tetrachloride (5 ml) was added and the mixture was stirred for 1 hr. The mixture was diluted with ether, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:4)) to afford 3.82 g (94%) of a white solid. m.p. 143-144° C.; 1H NMR (200 MHz, CDCl3) δ 1.40 (6H, d, J=7.0 Hz), 2.45 (3H, s), 3.60 (1H, m), 7.18 (1H, m), 7.25 (1H, m), 7.40 (1H, m).

Workup

  1. washwashed with water
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:4))

Sources & evidence

ORD record
ord-57a1990e797a4fde9166effef74bda72
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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