Triethylamine → 3-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzaldehyde oxime

HRID 426143Notes

Reaction equation

HRID 426143 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH:12]=O)[C:5]([CH:18]([CH3:20])[CH3:19])=[C:4]([Cl:21])[N:3]=1.Cl.[OH:23][NH2:24].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH:12]=[N:24][OH:23])[C:5]([CH:18]([CH3:20])[CH3:19])=[C:4]([Cl:21])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 591846443-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzaldehyde

Product 1

HCID 725369653-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzaldehyde oximeYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (69) (11.66 g, 35.8 mmol), hydroxyamine hydrochloride (2.98 g, 42.96 mmol), and triethyl amine (7.48 ml, 53.7 mmol) in ethanol (100 ml) was refluxed for 2 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:9)) to afford 4.5 g (37%) of a white solid. m.p. 185-187° C.; 1H NMR (200 MHz, CDCl3) δ 1.40 (6H, d, J=7.0 Hz), 2.40 (3H, s), 3.58 (1H, m), 6.94 (1H, s), 7.16 (1H, s), 7.28 (1H, s), 7.51 (1H, s), 8.10 (1H, s).

Workup

  1. temperaturewas refluxed for 2 hr
  2. customthe mixture was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:9))

Sources & evidence

ORD record
ord-25cfece2d59e4497966f0bf7b2c2926b
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…